Transcript

Sean: Jesse, what have you done so far today? 

Jesse: My day’s over. I got four kids under, under nine, man. I, let’s see. I ran seven miles. I took a ridiculously hot steam. I went in a ridiculously cold plunge. A cold, cold plunge.

I got my kids ready for school and played laser tag with them. I went over a bunch of work things that I have to do. I spent 30 minutes with my wife doing a little daily check in and here I am. 

Sean: Man, fantastic. You’re accomplishing more in those few hours than most people do in an entire day. Do you have the steam room and sauna set up in your house?

Jesse: I do. I do. Luckily, when we, when we bought this house. My wife was in charge of pretty much everything, because she knew that if she left it to me, there’d be no furniture. But, I was assigned Two things, steam room and sauna. And so, yeah, I got, I got that going. 

Sean: Two things I would love to have in my house when you’re doing the, the steam room, the sauna, the cold plunge, do you have a specific routine you do with that?

Jesse: I always end with cold. So, my routine is pretty much take it until I, until I have to tap out. And then with the heat and then go to the cold. 

Sean: How long are you lasting in the cold till you’re tapping out there? 

Jesse: Cold, cold I struggle with. But it wasn’t a soak. It’s freezing out today. And my cold plunge is like 39 degrees.

So I mean, that’s a dangerously cold. But I just, I was in and out. 

Sean: And then you mentioned your run. I’m still cold. It’s still shivering there. You mentioned the seven mile run. Is that pretty typical for you? That amount of mileage per day? 

Jesse: Depends if I’m training for something, like a minimum of six a day, I would say right now.

And, I try to get 10 in, like six, maybe six runs, four walk or five and five. I’m taking the next two months to kind of build a decent foundation and then I’m going to scale it up. I’m training for a race, so. What race are you training for? it’s called the last man standing and you basically run four mile loops every hour until, they start you on the top of the hour and you have an hour to complete four miles and change.

They line you up again at the next hour and they keep going until one person’s left. 

Sean: I love that. Just, just attacking life, taking on these challenges. A little over a year ago, you decided to take on a new challenge in your life and you lived at a monastery for 15 days. I want to know, what’s the idea behind that?

What were you looking to accomplish there? 

Jesse: Well, I, I just, I realized that I’d spent so much of my time, it was invested in physical stuff. I have a trainer, I run marathons, do these kind of crazy adventure races, et cetera. But I really hadn’t spent a lot of time on anything on the spiritual side of stuff.

So I decided that, you know, here I am, I’m turning 50, trying to be as well rounded as I can. And, I was like, okay, well, who, if I want to learn spirituality, like who would be the best, who are the spiritual masters? And everything pointed to monks. So I just said, I’m going to go live with a monastery. And that’s really, that was really it.

And, my publisher for my first book, Living with the Seal, had a relationship at a monastery. And when I brought up the idea, I said, that that’s what I was, I wanted to do. She made an introduction and, and they allowed me to come up. 

Sean: I’m picturing it’s like the 10 year old getting dropped off at summer camp.

Kid’s got a little nerve going on, pulling up in the bus. How’d you feel when you were pulling up there? 

Jesse: Just like that 10 year old. I mean, I was questioning it. You know, if it was, if I was, if it was single me,it would have been a different approach, but, you know, with the weight of my kids on my shoulders and my, my wife, you know, to be out of contact for so long, especially at that age, my kids were, you know, maybe I guess my daughter was a year.

Twins were three, two or three. So, you know, it was, it was challenging and, and definitely had no idea. I mean, I did, I went in blind. I did very little to no research on where I was going or what I was about to be in for. 

Sean: So when we’re thinking about the most uncomfortable part of that, is it the solitude, just being with your own thoughts for so long?

Jesse: That’s part of it. Part of it is just getting, you know, getting.Rid of, or not having your freedom, and I don’t mean your freedom like, obviously you’re free, you’re not under any kind of rule, but I couldn’t just pick up the phone and order Chinese food, or Uber Eats, or go to a movie, or put on SportsCenter, like all those luxuries that we take for granted are gone, so you lose the ability to say, this is what I want for dinner, or I want to go make a smoothie, or whatever, that kind of stuff goes away, so That was really hard.

And then also, there’s no clock there. Time stops. It just goes so slowly. And when you’re, when time goes really slowly and you’re looking at 15 days with no TV, no phone, no internet, no social media, no contact in the middle of nowhere, like isolated from world events. You start to get, you can freak out.

 so that, that was all part of the, part of the journey. 

Sean: During that time, did you reach a turning point where you didn’t start to freak out anymore and your mind went to a calmer place? 

Jesse: yeah. I, I did. I mean, it took me a while to get used to just the routine, the setup, the, in the, the monks, the personalities, their daily, the daily routine, the bed that I was in, how dark and quiet and cold it was.
all that stuff took time. And once. Maybe 10 or 11 days in, I started to settle in, but a little, a little of that was also that I knew that I was getting closer to going home. So I was really excited about that. 

Sean: So being able to live like that, eliminating many of the things out of your life, when you got home, what’d you end up eliminating out of your life that just made your life overall better?

Realize things that you might’ve been putting a lot of time into or using you just didn’t need anymore? 

Jesse: Yeah. well, it’s funny because I realized. A lot about what people ask me when I got back, like, what did you miss the most? What’d you miss the most? And it was really like what I didn’t miss. Like I didn’t miss watching TV.

I didn’t miss a lot of stuff that I spent every day wasting time on. no, I mean, I got home and I just definitely tried to simplify my life. Tried to like eliminate a lot of the decisions, eliminate people that weren’t moving the needle in my life, eliminate meetings that were wasting time, just. I became, the big fundamental shift for me there was Re establishing my relationship with time.
So like when we think of relationships in terms of people, you know, how’s your relationship with your dad or your mom or your kids or your friends, whatever. But we don’t think of relationships in terms of money and time. So I had a real appreciation for where I was in my life. I’m turning, I just turned 50.

I was turning 50 at the time recognizing that, you know, the average American lives to be 78. So if I’m average, I only had 27 summers left and how do I want to spend that time? And who do I want to spend that time with? And what are the things that I want to do? So I came back and I was like, man, I just want to put as much of the things that I love to do on my plate with the people that I love to do them with.

And that was, that was sort, that’s sort of been how I’ve been living my life since I got back. 

Sean: Are you more inspired right now because of the way you’re, you’re living your life? And then I also want to know, what have you identified as some of those key buckets you want to double down on and spend the most time doing?

Jesse: I’ll answer it in reverse order. So the, I recognize really, I only have four buckets. So I have, I have my family, my business, my wellness, and things that are important to me. I could be friends, that could be, Charity, charitable causes, whatever is important to me, if it’s not impacting my family, my wellness, my business or something that’s important to me, I’m not doing it.

And that’s sort of, I mean, of course there’s exceptions, but that’s really my rule of thumb. And I try to prioritize my time around those, those things. Now, your first question, I mean, I, what was the first question? 

Sean: The first question was about doubling down and spending more time on, on these buckets that you’ve identified.

Yeah. 

Jesse: And I am. I mean, I’ve always. You know, you, you’ve heard me talk before, so you know that I’m all about my life resume and not my, traditional resume. I’m always trying to build my life resume and put, have as many experiences and moments that I can. and I wouldn’t even say I’m double down on it, man.

I would say I’m quadruple down on it. I mean, I, I spend a lot of time planning stuff like that, looking for opportunities, trying to create newness. You know, as how old are you Sean? I’m 31. Okay, as you get older and you’ll see this like, you know, your 30s are a time where you’re still kind of You know, I guess you figured out what it is you want to do.

You, you know, you’ve had an interesting route through lacrosse and all the stuff that you’ve done. And now 30s podcast got this mega opportunity in front of you. But so you, most people is 20s. They tried a bunch of different things and figured out what it is they like to do, what they’re good at 30s. You perfect it 40s.

You really cash in 40s and 50s. You cash in on whatever, whatever that expertise is that you love to do that you’ve perfected. Maybe the trajectory speeds up now with the internet, but it takes time and yet, you know, it takes time to become great at what you do. And as I’ve gotten older, like, I want to be great at my life.

Like, I want to be great at putting on a, you know, Just unbelievable experiences and learning and continuing to grow and like and treating my friends and enjoying that with my friends and my family and like, that’s really important to me. Now, of course, you got to work, you got to make, you know, living and, and you have responsibilities.

I recognize that. But I doubled down, as you say, in those, in, in those buckets that are most important to me. I quadrupled down in those buckets. 

Sean: Absolutely love that mentality. I’m thinking about the average person. I feel like they’re not so focused on building their life resume and they’re getting more caught up in those mundane decisions and just experiencing decision fatigue.

I feel like you’re so clear and narrow in terms of what brings you the most joy. Do you experience at all some of those decision fatigue things about what you’re going to do today, what you need, things like that? 

Jesse: Yeah, I mean, I, I, like everybody else, man, I feel overwhelmed all the time. I mean, what I like to do is I like to get all my thoughts down on paper.

So I get it out of my head to free up energy in my head. I need it, I just want it all down on paper. It doesn’t mean that it’s done. It doesn’t mean that I don’t have to deal with it. But at least it lives somewhere outside of me having to remember it and using the energy to worry about it. And then what I do is I have like, you know, a daily, before I wake up, I go to bed for the next day, I have my daily schedule, so I’m not like, I’m not at a point in my life, I don’t think anyone is, even at 31, maybe at 20, but not even at your age, where you can just like wing it, like just get up and be like, huh, the hell am I gonna do, the fuck am I gonna do on this Wednesday?

You know, like that, that doesn’t work, man. If you look at all the great CEOs in the world, like most of them, most CEOs at a high level, they wake up and they have multiple assistants who hand them, here’s where you have to be at 10 o’clock at 1030. You’re done. Cause you’re going to take this call with Sean at 1030 from 11.

That’s that. And it’s all mapped out. And they just execute it. Now everyone doesn’t have multiple CEOs, multiple assistants. I don’t. So I do it myself. Here, here’s my day, you know, you’re like, you just, you asked me what I do today. That was already plotted out. That was done last night. I just had to do it today.

So it’s not like I’m in a scramble mode, like, Oh, you know, and I prioritize it by the most important things. And I attack my day like a fucking wild man. I mean, I have the stuff that I want to do. I take two, I take two to three hours every day for myself. Cumulatively, I make sure that I put, do the things that I like to do.

I map it out. I have time blocked out for things like this podcast calls, et cetera. And it’s all time for my kids. That’s from four 30 on. And my day is, is, you know, at least I try to make it mega efficient. And, and check all the boxes, but it’s not like I wake up and I’m like, huh, should I run today?

Should I? What should I do? No, it’s not. It’s already, it’s already mapped out. 

Sean: Attack my day like a fucking wild man. I absolutely love that, Jesse. When you’re talking big picture here, looking at that life resume, what are the biggest things you’re focused on currently? Big challenges you want to go after?

Jesse: So every year I had this, believe in this old Japanese ritual called the Misogi. Where every year you put at least one thing, well, one thing on your calendar so big that it changes you, that it impacts you for the other 364 days of the year. And so I haven’t scheduled what that’s going to look like this year, but that will be something.

But, um, what I’m focused on is I have a strategy. It’s not like. I have a plan. I’ve already mapped out my entire year now. I haven’t done this in the past. This isn’t like I, since I was 21 years old, I’ve been taking out a calendar and mapping things that have been highly efficient. I’m highly ADD, ridiculous ADD.

I’m ridiculously spontaneous. So I’m not mega organized. So I don’t want to, I don’t want to give the impression that this guy maps out everything. And he’s, but what’s happened is with four kids, With, you know, multiple businesses, multiple races I want to run, and a lot of different things fighting for my time.

I have been forced to create a new system. As you evolve, you have to, your system has to evolve with you. I can’t operate the same way that I operated when I, you know, when I was 40 with no kids. So I have to operate now in a completely different model. So for me, that looks like, you know, mapping it all out.

So the way that I approached that life resume thing that you, that you asked about. I have this thing, I call it Kevin’s rule. And Kevin is a police officer that I’m good friends with from Suffolk County. probably doesn’t earn, I mean, I have no idea, but I wouldn’t say he’s, he’s definitely not the wealthiest guy.

but he’s one of the happiest guys. And one thing that he does is every other month, he takes a trip either with his college friends. He’ll run a marathon. He’ll do something with his kids at a museum or something that he would do outside of the normal weekend routine. And I looked at that and I was like, wow, if I did that for the next 30 years, right?

I’m 50. So from 50 to 80, if every other month I took a weekend or one day of the weekend and created an experience. Then that means I’d have 150 experiences that I wouldn’t have had without doing that, right? If I was just sitting watching the Alabama game, which I love to do, or the Georgia game, or whatever, you know, every single weekend, well, if once every two months, instead of watching that game, I’m like, you know what?

I’m gonna go learn how to hunt, or learn how to ride motorcycle or take my kids to the art, whatever that experience is, I’m going to have 150 new things like that. So I’ve already mapped it all out. I’ve already mapped out those five things for the year. I’ve mapped out, you know, my big race. Like I just told you, the last man standing, I’ve mapped out my family trips.

So like my, my 2019 is ridiculous. It’s ridiculous. I’m doing a documentary. I’m writing a book. I’m running a major race. I’m taking multiple trips. You know, I’m doing it all. I’m almost operating like I’m fucking manic because there’s so much I want to squeeze out of life. That I don’t want to miss an opportunity.

So I’m operating like I want to do it all now while I can, who the hell knows if I could do it next year and that’s how I’m doing it. 

Sean: So this is the first year you’ve actually had that laser focus. This wasn’t like this in 2018. 

Jesse: Right. So no 18 again, I’ve, I’ve continued to accomplish things like this, but this year is the first year I pre scheduled it all and it’s already mapped out and it’s like, it’s, I took all the thinking out of it and in the past I would wake up and I’d be like, let’s go climb Mount Washington this weekend and get on a plane and wing it, you know, and it worked.

It’s worked for me. It’s definitely worked for me, but I don’t think, like I said, I, I’m in a new chapter of my life. A little bit older and I feel like that, that the system and the model has to, has to adjust with me. So, I actually brought in, someone, I, I’ve coined her a life optimization coach. And she’s worked with me to put together this amazing, what I think is a really, really amazing program, that I follow and I try to tell my friends about it or anyone who wants to listen on how to really maximize the year

So this is the first year I’ve really kind of put something in place like that. 

Sean: How does Jesse Itzler find a life optimization coach? You type this into Google? 

Jesse: No, the same way every single thing in my life has happened, like, wasn’t planned, I was looking, I was obsessed with goals. I was obsessed with, I, I was obsessed with trying to figure out how many goals, big goal, a, why do people, why do people accomplish goals?

And why do people fail in their attempt to achieve their goals? Like, what are the common traits? Of the successful people and those that fail, and there’s a lot, there’s a lot more that fail. I think it’s like 8%, 3 percent of Americans write down goals of those 3 percent that write down the goals, 92 percent fail.

 it’s a crazy, like the chances of, of hitting your, you know, your goals for the year is like super small. Well, why? So I started doing a lot of research around that to try to figure out what the commonalities are. And I read an article by someone, and this is exactly how my life works, and, you know, I read a lot of articles, but I read one article and I was like, who in the world, who wrote this?

I like this. So, I just like what she was saying, so I called her up, and I basically asked her to be my friend. And, literally four days later, she was at my house in Connecticut, and a day later, I hired her, and now she lives at my house in Atlanta. 

Sean: That’s unbelievable. This isn’t the first time, though, you’ve got a history of this, of seeing someone do something that catches your attention, and then reaching out to them.

When did you first start doing that? 

Jesse: I’m just drawn to interesting people. I’m drawn to people that do things differently. I’m drawn to, I don’t, I question the norm a lot, you know, like, I, I, there’s all these, I think normal is very broken and, so I’ve always been attracted to that. I just find those kind of people way more interesting and I enjoy spending time around people that think differently, you know, that’s like a really good, easy way to grow, spend time with people that aren’t, they always say like, Oh, surround yourself with like minded people.

For what reason? I mean, like, I already know how I think, so I’d rather talk to someone that’s thinking completely differently that I can learn from. I mean, I do have, obviously, a ton of like minded people around me, and I love it, but my point is I learn a lot from people that are nothing like me, the monks, the seal, this girl that just came to live with me, my wife, actually, all these different people, you know, really helped me grow.

Sean: Yeah. I’ve heard you mentioned a lot of these people before, like David Goggins, the seal. Is there anyone else that you maybe haven’t talked about so much that just made your hair stand up that they do things and think so differently that you were just immediately drawn to them? 

Jesse: Yup. a lot. Harvey Diamond.

He wrote a book called fifth for life completely. You know, blew up the whole notion around breakfast being the most important meal. That was really, an eye opener for me. I’ve been following his system for 27 years. I’ve only had fruit until noon, in the morning for 27 years on waiting. He’s someone I spoke to him yesterday that again, drew came, came to my, my radar screen and I cold call them.

And we became, you know, quite friendly and we’ve been friends for over, over about 15 years now, 10, 15 years. And that’s someone I still speak to. He’s someone that I would say is high on, on that radar. but I have, I have a lot of people like that. A lot of people like that. 

Sean: Constantly growing, constantly evolving.

You’ve talked a lot so far about challenges. When you’re identifying those, what, what’s been just the most physically grueling thing you’ve put yourself through? 

Jesse: Physically? Either the hundred mile run or I did a stand up paddleboard race around Manhattan. It took 10 hours, but that was really hard, really scary.

Just being out in the middle of the Hudson alone. I didn’t have a life jacket. I just thought I could potentially pass out because it was super hot, and I’ve never really been on a paddle board before like that. that was really hard. 

Sean: I’m curious that you mentioned that it was scary.

I feel like I haven’t heard you talk about that before. Is there a big challenge you’re interested in doing, but you are a little scared right now to take on that challenge? 

Jesse: Oh, you know, I’m not a thrill seeker, so I’m not the kind of guy that has to jump out of an airplane or put my life on the line just to get a thrill.

That’s that’s not me. I like endurance challenges. I like physical and mental challenges. 

Sean: what’s been the toughest thing mentally? I want to know when you’ve just gone through the darkest place mentally, what that’s like, 

Jesse: you know, I’ve been very, very lucky. That I’ve been very, very lucky. I, I haven’t had a tremendous amount of death, knock on wood or hardship like that in my life.

My parents are alive. my closest friends are alive and healthy. So, I, you know, the rea the life, the reality of life is to hit me in the face. Because I know that as I get older, that’s an inevitable thing. And I, I’m very, again, going back to my relationship with time. I’m very aware of all those things.

I don’t, I don’t hide behind, you know, I’m aware of the fact where my parents are in their life, where everybody in my life is important to me is. So, that helps me dictate how I spend my time with them and my conversations and trying to be super present when I’m with people, you know, that, that are older or important to me, et cetera.

So, but I haven’t had. But I’ve had some, I definitely had some challenges. you know, nothing I want to really share with the world. The, the, the darkest stuff I don’t really want to share with the world, but I don’t know how I got through it. I don’t know. I probably should 

Sean: have worded the question differently.

I wasn’t talking about some of those personal things. I’m thinking about reading your book, Living with Seal, and certain challenges that Goggins put you through. And I know you’re challenging yourself out there on the mountains, things of that nature. What, what comes to mind when you think about that? 

Jesse: I mean, the 100 Miler was the hardest because it had the most pressure on me.

Because I, I had, raised a lot of money everyone in my world knew about the race taking in well over a million dollars in donations from over 3000 people. So I had a lot of pressure to finish it. And so that was a really hard thing and, just, it’s just the, that kind of pressure is difficult.

Do you experience pressure a lot? I love pressure, man. I love pressure. It’s like my friend, Tim Grover says, pressure is a privilege. I love, yes, I, I don’t have to, I choose to have it that’s part of it, man. That’s part of, that’s part of great things happen really only after you have a little pressure.

You know, so I, I like to have pressure on my plate. 

Sean: I’m thinking about pressure and then I’m also thinking about the limits you can push yourself to. I, I know you learned a lot when you had seal live with you. What did he teach you about the limits you have in your head and how you’re capable of so much more?

Jesse: Well, I got to watch him and be around him and that was very infectious. when he lived with me, I’d already ran a hundred miles. So I, I, when I already gone from. My goal of two miles that was my goal at first to run two miles nonstop and I had taken it all the way to 100 miles so I had basically, I’ve been under indexing 50 X, right?

My goal was to two miles and boom, I ended up at 100. So I started thinking like, well, what are the areas of my life? I might can I get 50 X the results, right? Like, yeah. Are my sales numbers too low? Like maybe I should be selling 50 times as much. Maybe my revenue target should be 50 times as high. I started thinking a lot about that.

but when guys came in to my house, I just like spending time with the man, you know, and I was like, I just wanted to, I kind of committed to the process for 30 days. He lived on and off our family for a long, way longer than that. He was part of our life for a long time. but during the actual kind of initial training period, I kind of just, I said to my, I realized that I would never have this opportunity again.

So I was, I was fully committed to it. 

Sean: You talk about under indexing and that you’re capable of 50x more. After living with him, what other areas in your life were you under indexing in? 

Jesse: all of them. I mean, I real, I was operating at that point pretty high level, man. We, my business, Marquee Jet was my business.

we might’ve sold it. I don’t remember exactly the timeline, but, but, you know, things were good, but I realized that like, I could, I could do more in everything I was doing, even though I was, I thought I was operating at a pretty high level across the board, again, a hundred mile run, successful business, multiple businesses, great relationships.

But again, I think the only way you can rate yourself is against yourself. So I had to look inside me and be like. You know, to the outside world, maybe it looked like a high level and but to the inside world, it’s not about high level, low level. It’s like, personally, can I just do more? You know, like, am I capable of more?

And do I want to rest after this marquee jet experience? Or do I want to step on the gas pedal? 100 mile run or do I want to step on the gas pedal? And, you know, he’s, his foot’s on the gas all the time and my foot, I can’t have my foot on the gas all the time. I, there’s too many, too many things in my life to, to, to do that.

But I realized that when my foot’s on the gas, I could step a little harder. 

Sean: It’s almost like your total RPMs, you keep building them up, isn’t it? Yeah. So when you sell Marquee Jet. I know you’re a check the box kind of guy, what’s that like at that moment? Are you happy? Are you elated? Are you sad?

Depressed? Are you thinking about the next business? What’s that like? 

Jesse: I think it’s different for everybody. I was never super duper connected. It wasn’t my identity. I wasn’t, I mean, it was my business. And I wasn’t super, it wasn’t my life and I loved it. I put a tremendous amount of time into it, but I had a lot of other interests and things that I wanted to do at that time.

So I celebrated it, but I was celebrating it for the nine years prior. I was celebrating all the wins along the way and, and actually celebrating the losses too, you know, like, or taking inventory of the losses. So I was, I was along for the ride the whole time. So when, when that moment came, when it was time to, for Mark, when Mark, he got sold, I was already celebrating all the baby steps it took to get there that it wasn’t like this ginormous celebration.

You know what I mean? We, we were doing well. We were, we were, I was making, I was earning a great living and, it wasn’t like this monumental day. I’d sold two companies before that, so I’d gone through that process. I remember the first time, the first company I had was called Alphabet City, and I was super young.

I started it like, I don’t know. I think I was like 24 or something. We sold it to a public company called SFX for stock and cash. And I was making 33, 000 a year living in New York. So I was basically losing 4, 000 a year. but until we sold the company and I remember sitting there, signing all the documents, they were laid out on a table and I was young, young.

I was in my, somewhere in my twenties we were getting a. What was all the money in the world to me at the time, millions of dollars. And I remember sitting there with my partner and we signed all the documents. There’s hundreds of pages that we had to sign for the closing. And the guy on the other side of the table that was, that was buying our company, when they were all done, picked up the phone and he said, the three magic words, man, all he said was, send the wire.

And I looked at my partner, I was like, I looked at my partner and I, dead in the face. And I said, Send the fucking wire. And that was it. It was a hell of a moment. And I remember going to my bank to my ATM. The I lived in this very, very, very small apartment in New York. And I remember about a year before I had gone to the ATM machine, and I knew I had no money in it, because I only had about 118 in my bank account.

And I went to pull out like 200 bucks to go out for, for, a trip that we were taking to, I think New Jersey, Jersey shore. And, but I knew I only had 118 in there, but it spit out, 10, 20 bills. And I was like, what the, what is this? So I put my card in again and it spit out 20, 10 bills. And I did it all the way to 1, 000 and said, you’re at your limit for the day.

And I was like, I said to my roommate, I’m like, we got to go back to this machine tomorrow. I’m like, cancel the trip. We’ll go. So we went back to the ATM machine and it spit out more 20s until I was done for the day. And then it stopped. And I was like, this is unbelievable. I got like 2, 500 free dollars.

Until I got my bank statement and said that I had a credit limit that I didn’t know about, a credit line that I didn’t know about. So I went back to that same machine after the sale and right where I live, and I remember waking up the morning after the sale and seeing that I had earned 500 in interest overnight.

And I was like, what? I made 500 sleeping last night. I’m like this, I’m going to sleep the rest of the year. And, so that was a much bigger celebration. Even though the numbers were a lot smaller than, than the other stuff, because it was the first, 

Sean: it was the first, and it was also a short time after you had just been sleeping on couches.

You tell this unbelievable story. I would love for my listeners to get a chance for you to tell this about sleeping on a girl’s couch and getting to meet her dad, the mogul. Do you remember the story? 

Jesse: Of course, I think about it every time. 

Sean: This is one of my favorite stories, and the advice out of this is just so unbelievable, so I’d love to hear you tell this.

Jesse: Yeah, I was, again, I slept on, I think, around, I think it was 18, I’ll have to double check the math, 18 different couches between 19 and 22 of friends that put me up while I was trying to figure out my way in New York. In the music business and trying to figure out what I was going to be and, one of my friends kicked me out and said, look, my parents are coming.

I love you, but you got to go to someone else’s couch on Monday. So, rather than go look for a place to stay, I went to a bachelor party in Jersey in Atlantic City that weekend. And at the bar, I met a girl, not met a girl like met her, I was just online to get a drink and she asked me what I do and I said, Oh, you know, she asked me where I lived and I said, Well, actually, as of Monday, I have nowhere to live.

And I told her, you know, I’m sleeping on my friend’s couch and this and that. And she said, joking around, she says, Well, if you get stuck, and you’re in, it’s an emergency. Here’s my address. And she wrote it down on a napkin, and she handed it to me. So Monday morning comes, and my friend You know, says you got to go and I’m like, this is an emergency.

So I, I showed up with my one duffel bag of all my stuff that I own at her, at her apartment and at about 8, 8 30 in the morning before she went to work and said, I’m in an emergency. And I ended up living with her for six months. And as it turned out, she had a roommate, so I slept on the couch, they each had their own room and I slept on the couch.

And her father, as it turned out, pure coincidence, was a, was really like a mogul in New York. he owned a piece of the Yankees, a piece of the Nets, he owned a thing called, a garage called Kinney Parking Garage, one of the biggest parking garages in New York City. And I was at a, I was at a turning point in my life because, I just wrote the song for the Nets.

And I was writing theme songs for other sports teams or trying to, but everything was on was off of kind of, I had to pitch them. I had to, I had to, what’s the word? It was like on the comp. I had to, I had to present the song and they would either buy it or not buy it. That’s what I was doing. I was writing theme songs for sports teams and I would do them in the studio, say to the Dallas Mavericks, Hey, I wrote this song.

Do you want it? And they would say, yay or nay. But I had to, yeah. I had to spend the money in the studio, it was on spec, you know, and they would either like it or not. So I needed the money to go in the studio, I had no money, zero. So I went to see this guy, so this manager, music manager I went to see said, I’ll give you the 10, 000 you need to go in the studio for 10 percent of all your future earnings.

And I’m like, Don, that sounds like cool. You’ll give me 10, 000 and I need, and the only thing is I got to pay you 10 percent as I earn it. I was like, I don’t have any other options. So I’m like, before I take it, Fran, let me talk to this girl’s dad. So she set me up with the meeting. I go to this guy’s house, penthouse on 57th street, Sutton place.

And as soon as I walked in, it was like Daddy Warbuck shit, you know, unbelievable paintings on the wall. He has a lap pool, in, in his apartment. I mean, it was just bananas. And I go in to talk to this guy. And he comes out of the swimming pool, the whole thing was nuts. He comes out of the pool naked, gets on a treadmill, we’re having this conversation.

I mean, he was crazy eclectic, but a genius. And, I said to him, I told him the whole situation. And he said to me, you know what, Jesse, I would trade the one, everything that I have for the one thing that you have. And I was like, I have nothing. What are you, what are you talking about? What’s that one thing?

And he said, you have the, you have youth. You have the whole process and journey in front of you. And this one decision, it’s just part of the journey. You’re going to have a lot of decisions like this. I’ve already, he already did it all. It wasn’t the thrill was gone. Just like when Marquis, when the wire hit.
It’s not, it doesn’t taste as good necessarily. He already did it all. He wanted to go back and be on the path that I was having it all in front of me, you know, and, a big canvas to paint on. And that man that struck a nerve with me because he had what I thought was everything. He had everything. And then he said to me, you know, before you take the money, he’s like, are you, can you make this work?

No, he goes, will you make this work? You know, will you make this thing? Would you bet the farm on this business? Will you make it work? And I was like, I know I can work. And he’s like, that’s not what I asked you. I didn’t ask, can you? I said, will you make it work? And I go, yes, I definitely am going to make this thing work.

He’s like, man, the fuck to 10 grand, go figure it out. And I was like, okay. And I did. 

Sean: Was that the most fundamentally shifting conversation you’ve had in your life? 

Jesse: Well, that was 30, 30, 29 years ago, and I still think about it all the time, but what I think about is as I get older, it’s less about the, will you make it work test?

And would you bet the farm on this idea? Do you believe in it that much? People always confuse passion with their real true gut belief, like, you know, like seeing the movie, seeing the end of the movie in their head and knowing they’re going to get to that end destination. They confuse that with the passion and the excitement around the project or whatever it is you’re doing.

You gotta see yourself on the podium, man. You gotta see the finish line and know you can get there. And don’t get fooled by the enthusiasm, because everyone’s gonna want to dive into something. And I knew I was going to make it work. I saw it. I saw it clear as day. You know, there was no B plan. but the lesson that I learned wasn’t about that.

The lesson, although I do think about that all the time, like I bet the farm on this project to make it work. The real lesson was like how he was older. And as you get older, you know, you become less relevant. And your window to do the things you love to do shrinks. Man, you’re not in that right now. I’m living it.

I’m living it. And I said to myself, I don’t want to lose my 30s. I don’t want to lose my 40s. I don’t want to do shit that I don’t like. I don’t want to work for someone I don’t, where I’m not happy. I’ll take less, you know. and that, that always guided me. Like, I always. That’s always been something for me, like just doing things I like to do.

It’s worked out for me financially, but even if it didn’t, I’m just as happy as I was. This is going to sound crazy, man, but I’m just as happy as I was when I was, when I left his door that day. I’m just as happy as I was now that there was no, there’s no difference because I’ve been doing what I like to do under my own terms, taking time for myself during the day.

And I still, even though I have the ability to do it, I still live relatively simple, you know, I run, I get in a cold box, I do races, I paddleboard, you know, I, I, those are the things I like to do. I’m not, I’m not spending my time in museums in Italy. Nothing against that. I’m not spending my time on giant cruise ships with suntan lotion on me, you know, and reflectors on my face.

Nothing against it. But I’m doing the stuff that I’ve been doing just on a bigger scale since I’m 21 years old because that’s what I like to do. I

Sean: absolutely love that. You talk about seeing the movie in your head. I’m sure the listeners are wondering when this guy got out of the pool, did he change prior to going on the treadmill?

Jesse: Hell no. The answer is no. 

Sean: That must have been one hell of a scene.

Jesse:  This guy was nuts. He was the best. The best. The greatest guy. The most generous guy. You know the expression, they say that money’s the big magnifying glass. And if you were, if you, it just, it just, it just shines a light on you and makes you more of who you are.

So if you were a nice, generous guy, once you have money, you become more generous and nicer. But if you were a dick, you become a bigger dick. This guy was Mr. Generosity. And I remember going to his funeral and, he died in a plane crash. I, and, and multiple people told stories about things that he did that no one ever knew about.
You know, helping people, helping waiters, helping the doorman, helping a stranger, there’s just dozens of those stories you know, he passed the magnifying test. 

Sean: It’s great to hear about people who are so successful in what they do, but have the type of impact he had on you and what it sounds like so many others.

I’ve heard you talk about a Harry Truman quote, if you can’t convince them, confuse them, and how this has kind of been a reoccurring theme throughout your life. How did this quote impact your rap career and getting in the door? 

Jesse: Well, I had no connections. My dad owned the plumbing supply house. I didn’t know anyone really connected in anything.

Any business, anything, not like I, we had no connections to get into college or to my dad. It was just very simple. So, I had to rely on myself to, to get a record deal. I didn’t have a lawyer. I didn’t have anyone shopping and I didn’t, I didn’t have a manager. So I would pick up the phone and it’s, there was no email then.

So the only way to get someone was to get them on the phone. So I became really good at it and I used a technique called confusion. I would just say anything until something clicked. And as soon as something clicked, I would ride until the next train stop. And, that’s how I got into Delicious Vinyl, the label that ultimately signed me.

I knew that the owner was a friend, was a big fan of this rapper named Dana Dane. And I said that, I actually work with Dana, so I said, you know, I work with Dana and used that trying to get into the, to get on a call with the owner. And his assistant put me on hold and she confused it. And thought that I was Dana.

And she said, look, if Dana, if you come in at two o’clock, you know, Mike would love to meet you for some lunch. So I took the opportunity to be Dana, Dana two o’clock and, and showed up at the office. And ended up getting a record deal. 

Sean: Just confusing them, getting ahead. It’s so great to hear about how gritty you are, what you’re willing to do, the life perspectives you’ve had.

I’m curious, looking through your lens and identifying true greatness. When’s the last time you’ve seen true greatness? 

Jesse: I mean, I see it all the time. I see it all the time. I am very lucky that I’m exposed to people that are the best at what they do. And, you know, I was talking about that earlier on, right?

Try different things in your 20s, figure out what it is you love to do in your 30s, and perfect it. Become an expert, and then monetize it. And, I’m at that age now where people that I’m around have perfected, they’re the best at what they do. And, you know, I’ve become friends with guys like, I don’t know, Sanjay Gupta.

Who is just, I mean, these guys are just so good at what they do. Harvey Diamond when it comes to wellness, you know, so I’ve been exposed to some of the, and even just teachers in my son’s schools, I’ve seen some amazing educators, some amazingly passionate people, you know, superheroes and mentor or mentors don’t have to be superheroes.

They don’t have to be the people with a million followers on Instagram. They don’t have to be people. You know, the people that I most look up to are very blue collar, you would never think, and those are people I go to very often for advice, not these gurus that you see all over the place promoting themselves in this net.

Superheroes, mentors don’t have to wear capes, man. And these experts, the best in the field, they’re, they’re sometimes very quiet. Sometimes you find them in the weirdest places. Look what, look, I have a girl living with me right now that I found off of reading an article that she might not be an expert to everybody else.

But she clicks with me and it, and it works for me. So she’s my expert, you know, the other 7 billion people on the planet that she might not, she doesn’t have a degree. She’s not even trained in this. I coined her the life optimization coach, you know, as a new gig. But, for me, she’s my expert. 

Sean: When we think about experts, this is going to be my final question.
I know you got to take off here in a minute. I’ve really looked to you from a business perspective, challenging in life. But the thing I admire you most for, from an outsider’s perspective, it seems like you could be one of the coolest dads I have ever seen. And the joy and passion you fill your house with.

I’m a father. I’ve got a five month year old son. What should I be focused on? 

Jesse: Oh man, I, you know what? I am just having a blast with it. I’m enjoying every minute. I operate from a place of like, I feel so damn lucky. That I, I have kids. I work really hard to get kids, to bring them into the world. And, so, nothing’s a pain.

Changing a diaper’s not a pain. Getting up when they have fever isn’t a pain. my kids want to go today. They want to play laser tag this morning. We talked about it at the top of the show. It’s the last thing I wanted to do. And I, but I did it and it was super fun. So, for me you know, I’m always trying to be super present with them.

I’m trying to be where my feet are, which is always a challenge with my phone and this and that, um, but kids and they need their, they need their moms and dads, man, they need, they need it. They want to be heard. they want to be loved and I’m enjoying it. And you know, Sarah and I have a bunch of rules that we use, but it’s like with our philosophy on how we want to raise our kids.

try not to over schedule them. We try to praise their effort as they get older. You have a five month old, so your effort’s going to be like, great, great job trying to stand up. But, in a couple of months at least, but as they get older, you know, it’s, we really trying to emphasize. the effort, but I, I would say this, if I had to really kind of sum it up is the hardest thing for me is, and look, you played lacrosse at a super high level, your, your child, I don’t know if you have a boy or girl, but your child might not be into lacrosse.

They’re on their own journey and recognizing that they’re on their own journey and, and even though I played basketball every day in my driveway till my mother made me come in for dinner for, for bedtime, and my son wants to play fortnight. I, that’s it. It’s his journey. And that’s a really hard thing to separate.

But it’s, I think it’s also a really important thing to understand. 

Sean: Absolutely incredible advice. I don’t think we could pick a better spot to end on there, Jesse. I said at the top of the show, it’s been a year and a half in the making. You’ve been the number one person I wanted to have on this podcast, so I am so honored and thrilled we finally got you on.

I truly can’t thank you enough, but where can the listeners stay connected with you? I know you have some big events going on coming up. Where should they be checking out? 

Jesse: Yeah, no, thanks. so I’m on, on social Instagram at Jesse Itzler, my name. My website is jesseitsler. com and everything is up on there.

Sean: Well, thanks again for joining us on what got you there. 

40:03 Sean reads an excerpt from his book, Masterpiece In Progress: A Daily Guide to a Life Well Crafted

Masterpiece in Progress is more than a book; it’s your daily companion in the art of living magnificently. Are you ready to begin crafting your masterpiece? The journey starts now.

I’ve poured everything I have into this book, with the aim of making it your go-to resource in the art of living a magnificent life.

Checkout what people are saying about the book:
“Intensely positive and upbeat, Sean DeLaney crafts a master class in personal development. This book is about the art of AMPing up your life.” – Frank Slootman, CEO, Snowflake and author of Amp It Up

“The brilliance of Masterpiece in Progress is its ability to impact us all and in all aspects of our lives, whether you’re an athlete, entrepreneur, author, aspiring executive, parent, friend, coach or mentor. Sean’s insights light your path as he delves deep, providing not just inspiration but tangible tools to help you craft the life you envision. A masterclass in self-growth and a must read.” – Scott O’Neil, CEO, Merlin Entertainments and former CEO of Philadelphia 76ers and New Jersey Devils

“Operating in some of the world’s most challenging environments, I’ve seen firsthand the importance of grit, resilience, and relentless pursuit of excellence. Masterpiece in Progress embodies these principles, offering a roadmap to all who aim to conquer their personal and professional battles.”— Michael Burns, US Navy SEAL (Retired), Bronze Star Medal with Valor

“Sean’s beautiful, thoughtful writing reminds you what’s important and calls your attention to a perspective that lifts your spirit each day. Highly recommended.” – Derek Sivers, author, sive.rs