The Resilient Mind - Why Realistic Thinking Is Holding You Back - Jesse Itzler

Episode Date: September 26, 2025

In this powerful episode, entrepreneur, author, and visionary Jesse Itzler reveals why playing it safe is the fastest route to mediocrity. Known for co-founding Marquis Jet, partnering with Zico Coconut Water, and co-owning the Atlanta Hawks, Jesse’s life is a case study in what happens when you abandon "realistic" thinking and aim for the extraordinary.Take action and strengthen your mind with The Resilient Mind Journal. Get your free digital copy today: ⁠⁠⁠⁠⁠https://bit.ly/Download_Journal🌍 Proud member of 1% for the Planet — building resilient minds and a resilient planet.This episode was created in partnership with Tom Bilyeu. Subscribe to Tom Bilyeu’s channel for more inspiring speeches: https://www.youtube.com/c/TomBilyeu Hosted on Acast. See acast.com/privacy for more information.

Welcome to the Resilient Mind podcast. In this episode, you will be listening to why realistic thinking is holding you back, with Jesse Itzler. Get access to the Resilient Mind Journal by clicking the link in the show notes. Enjoy. Well, I realize that experience takes too long. I don't have enough time for everything I want to do to get experience. No, I just realized that I'm an adrenaline junkie. I love newness.

I love challenges. I mean, that's what makes me feel most alive. And I discovered that early on when I was trying to get a record deal and just getting rejection. I had no connections. My dad owned the plumbing supply house in Long Island where I grew up and we weren't connected to the music world. And I just loved the thrill of trying to do what everyone said I couldn't do. There's no way you can, you know, all my roommates in college were writing their resumes and sending it out to all the companies.

They were like, why aren't you writing your resume? We're all like typing a resume. Why aren't you working on it? I'm like, because I'm going to get a record deal. And when they said, no, you can't, it just fueled me more to want to go out and get it. So in that moment, and if you can get people to understand this, like you will help so many people break through, because it is that moment where people tell you that you can't do it, and you don't just thrash and say, watch me, watch me, you really go out and do it and get really clever about it.

And so there's two stories to me that parallel. There's the muffin story and how you launched Marquis Jet, which I thought was absolutely fascinating. And then there was how you talked your way into getting the record company Delicious Final to listen to your demo. Sure. So, well, the Markey Jet story, you know, my partner and I were guests on a private jet when I was 27 or 28 years old. And when we walked onto the airplane, it was like the scene in the Wizard of Eyes when everything goes

from black and white to color. We're like, people fly like this. This is unbelievable. I want to fly like this. And by the time we landed, we were like, let's start a private jet company. You know, like, definitely. So we could fly privately, except we had no airplanes. So we went to a company called Netsets, owned by Warren Buffett, the 800-pound gorilla.

They had 600-plus airplanes in the fleet and pitched this idea for a 25-hour prepaid jet card, which was called Markey Jet. How did you get that interview, like that time with him? It's a crazy story. I had a friend of mine who called me up, and prior to that, I was putting experiences together for wealthy people, like impossible to get experiences. And a friend of mine called me up and said that he had a friend whose daughter was turning 16 and he wanted to do something at the Christina Aguilera concert.

And I happened to have a relationship with the management company. And I got his daughter on as kind of like a backup singer kind of thing with the mic off. And the guy called me up after the concert. Like the next day she was the star of the town. You know, everyone was talking about it. And he was like, I have no idea who you are or what you do. but if you ever need anything, call me. Like, that was amazing what you did for my daughter.

And it turns out he was the president of this company called Nets that owned all these airplanes. So a year later, when we had this idea, I was like, I think I know someone in this business. You're like, the guy that we had to sing his daughter sang at the Aguilera concert. And that's how we got the meeting.

Wow. But the meeting, actually, when we pitched the idea, the meeting lasted 12 minutes and they threw us out. And the president of Netsets said, and this is almost a direct. He said, you know, cool idea, but if you think we're going to give two kids that didn't break a thousand on their SAT, which Tom pissed me. I got like a 980, but I've convinced myself, I've gotten over here.

Keep telling yourself you broke a thousand. He's like, I'm never giving you guys access to our airplanes. Because the notion was if we could sell and market onto their fleet through this 25-hour program called Marquis-jet, that's how we would piggyback with their airplanes. And they threw us out of the meeting. And then we were relentless and we came back and we realized that we couldn't sell this concept through a PowerPoint because they'd seen a thousand powerpoints a month. So we literally brought our own focus group in to bring the meeting to life.

And one by one, the guys stood up. We had Carl Banks from the New York Giants and run from Run DMC and a powerful real estate mogul and they explained that they would never buy a fraction what Netjet was selling, but they would buy a 25-hour card if it was all. offered. And that's how we ended up solidifying the opportunity. And then to your point, when we started the company, you know, this is back in 2000. So there was, I had no sophisticated way to get leads. I didn't know a lot of wealthy people. And the only way that I could really build my database or sell anybody was to go to events where rich people hung out. So I heard about

this conference called TED. I didn't even know what it was in Monterey, California. So I flew commercial, you know, transferred three flights that drove six hours when I landed to get to Ted to try to pitch this idea to anyone that would listen. But when I got to the TED conference, it was like Fort Knox. Everybody had credentials, double credentials, and I had nothing. And they wouldn't let me anywhere near the venue. So I went to the local coffee shop and just trying to figure out how I'm going to get in or sneak in or get someone to get me in or get access. And I realized Like every hour or two, everyone with credentials was walking into the coffee shop and they were buying lattes and muffins and lattes and muffins and lattes and muffins.

So the next morning, I woke up at 5 o'clock and I went to the coffee shop and I bought every single muffin that they had. I took all the inventory out of the shop. I'm like, I'll take all your muffins. They gave me like 80 muffins. And I was sitting and then when the first wave of TED attendees broke for their break and they came. One of the customers said, you know, can I have a latte and a muffin? And the guy said, well, I'll give you a latte, but we're all out of muffins. And when he was walking out,

I said, excuse me, sir, you know, look, I happen to have an extra muffin. Actually, 800 of them, you know, but if you want a muffin, you can have one of my muffins. It's like, no, get out of here. So, no, is I realized that we started, well, what do you do? What are you doing here? We started having a conversation and he said, you know, do you mind if I join you? And I, you know, But my only thought was like, you are qualified to buy a card, you can join me. And he was my first sale. He was my first sale, a guy who owned a company that sold it to eBay. And that was the start of the adrenaline rush of, okay, let me try to crack this code of, you

know, how we can build this thing with not a big database. How do you teach somebody to look for those opportunities, to create those opportunities, because everyone's going to hear the no. But 99.999% of people just accept it. I think it's different. I think when you're young, the consequences don't matter as much. You know, you're just thinking about the end result. It's a little bit different now.

I have four children, and I don't think I could take the risk necessarily that I did when I was 21 and living check to check. But at that point, the consequences didn't matter. If I had to get thrown out of the TED conference or whatever, it didn't really matter. I would just try again. But it's always been having, for me, it's been probably similar to you when you started your business, but it's always having the end of the movie in my head and then filling in the script. So I knew I was going to leave there with a sale.

I just had to write the script. And the script might change. There might be, you know, call an audible and you might have to rewrite the script. But the end of the script was always the same. I'm going to run 100 miles. Okay. Well, how are you going to do that, Jesse? You know, like, you've never, you're not like a crazy endurance.

runner, well then let's think backwards. But it starts with the end scene in the movie, even the exit. You know, like, okay, we're going to build this to sell. I don't know who I'm going to sell it to. But that's sort of been always kind of the mentality. And I think the second point to that is once you get over the fear of being embarrassed, no one likes to be embarrassed. But once you get over it being scared of being embarrassed, it's super liberating.

And it allows you to go into lanes that otherwise you wouldn't go into. And everybody's wired differently. You know, everybody's wired completely different. It's hard to rewire someone to be, you know, comfortable at taking risk, comfortable with being embarrassed. And I think it comes from having a lot of egg on your face and learning along the way. I've always been like, let me get my foot in the door and I will figure it out. I will hire people that can help me figure it out. I can go to experts to help me, but they usually won't help me get in the door. So let me take the first step.

And then once you have momentum, you can ride the momentum. So that's always been my MO. You know, it's always been in everything. You mentioned living with the seal, you know, when Goggins came, all that stuff. It's just been like welcoming the unknown and being open to whatever comes of it and learning from it. Well, networking has been a big part of my life forever. When I was 24 years old, I wrote 10 letters a day, thank you notes, to anyone that came into my life that impacted me. And it could be, even if I didn't know you, but I saw your show and I was like, you know what, Tom, you've had some amazing guests.

I've really benefited from. I would just write you a handwritten note because, one, the handwritten note shows intent. You have to buy the envelope, buy the stationary, write the letter, lick the envelope, get the stamp, put it in the middle. That's a lot different than him send. It's also memorable. How many handwritten letters have you gotten this year? So I literally wrote 3,000 letters in one year. And it could be to a doorman, a cab drive.

It could be anyone. I would just get their car and I would thank them. That was my form of networking. Even to this day, I have a hot 50 list of 50 people that can help me, that I want to stay in touch with, that I make sure every quarter or so I send them a note. And they always comment on it. You know, like, thank you so much.

And it's authentic. It's not, I'm not just writing it to write it. I mean, they have to really have had an impact on me. And it's a meaningful note. It makes me feel great. And it makes the recipient feel attached to me in a different way. You know, at an early age, I understood the importance of that. The people that you meet in your 20s rise up in their 30s are in great positions of power

in their 40s. You don't know when you're 20 in your 20s who's going to make it and who's not. So, you know, you treat everybody properly and respectfully and you stay in touch. And very often those relationships merge their heads years later, decades later. Yeah, I think, well, with Gagins, this was his first 100-miler. And I was doing it as a relay race. So I was doing it with five friends. He had no one to relay with.

Like, he was his only friend at the race and he was his own team. And immediately I was drawn to him because, you know, he was a super, he was a heavyset at the time. really muscular. And I was thinking, like, how's a guy that weighs this much going to run? His goal was 100 miles, you know, and he had no supplies. It was a self-supporting, you had to bring all your own supplies. I just sold my company to Warren Buffett. I had like way overdid our supplies. I had misuses and a whole food's truck pulled up, you know, and like Gagins had a glass of water, a box of crackers, and like, you know, a chair. At mile 70, he went through this, he had crushed his feet, you know, he broke several bones. And I watched. I watched it. And I watch,

watched him get up and continue on. And I was like, what the fuck is going on here? And when I was done, I'm like, I gotta meet this guy because, and nope, at this time, he was relatively unknown, you know? This is 2007, six or seven, I think, something like that. And I wanted to meet him because whatever drive, whatever got him off the chair and said, I want to keep running. If I could teach that to my kids or to my employees or to my six.

self. Like, I want that secret sauce. And initially, you know, I went out because I saw a lot of star power in them. I saw just a whole, just different world. You know, he represented something I'd never really seen before. And I realized that I wasn't going to get that secret sauce through a friendship or at a lunch meeting or this and that. And then I asked him to come, you know, would you come live with me? And basically he said, if you're crazy, you're crazy, enough to ask a guy like me to come. Motherfucker, I'm crazy enough to come. And came to my house.

That's awesome. I love that. Is that something that you do with frequency to, you'll see something, be curious, be interested, and do more than just the, you know, the casual, hey, it's nice to meet you? It is. I mean, if I find someone that's inspiring or an event or something, I try to introduce he, she, or it to my life. And that's part of just my own personal development.

You know, I'd learn better through experience than through books. I like to be challenged and I love interesting people. I like people that think differently, that act differently. That's what attracts me. That's just what makes me feel like I'm getting the most out of life, you know, and that is, I'm on a constant search for that because I'm very aware of my own mortality. You know, I'm 50 years old. I'm turning 50 and the average American lives to be 78. And if that were the case and I was average, that means I got 28 years left. And that dictates, well, who do I want to spend that time with and what do I want to do? And that's a driving, you know, it's like on repeat in my head.

So to answer your question, you know, that's sort of what makes me tick. And you've got a pretty deep obsession with that. At one point, I think you were writing the number of days that you had on your wrist or something like that? I stopped doing that. Why did you stop? I'm curious. I'm just so aware of it now, you know. It was starting to freak my wife out a little bit.

It's a little depressing, but for me, it's not depressing. It's like, you know, I think people's relationship with time. We talk about relationships with humans. How's your relationship with your kids? How's your relationship with your wife? You know, your dad or your parents? But we never talk about a relationship with money and time. And your relationship with time is such a key component of your life.

Because when you get caught in a routine, time goes so quickly. When you understand that there are maybe only 28-some... is left. And if you want to truly, you know, get as much out of, experientially out of life, it just creates a tremendous amount of urgency. So, and the fear goes away. Because you're like, shit, man, nobody on the planet, like, everybody, no one's going to be here in 100 years. Do I care what he thinks that, like, he's not, we're not going to be here in 100 years. So why when I take the chance? And it's just, I don't know. It's just so, I stopped writing it because I'm so aware of it. There's not a day that goes by when my head

it's the pillow where I don't say to myself, like, you know, did I maximize the day and am I, and, you know, am I aware of my mortality? And it might sound depressing, but it's, it's not. For me, it's, it's thrilling. It's thrilling. I mean, I think easy's boring is an easy answer to that. I think that it goes to your point of building your life resume. You know, we spend, we invest so much time in our work resume, which is important. But I think it's equally, not more important to build your life resume because that's really an indication of who you are and what you're becoming. And that's really a true look into your true body of work. So I lived on a monastery with eight monks, four of which have been there for 50 years and 50 years. And I went there

for 15 days. I think, you know, the obvious takeaways were just the simplicity of how the monks live is something I think everyone can benefit from. I realize immediately, you know already what you're going to miss. You're going to miss your family and your kids and your friends and some of the comforts. I don't want to give away

some of the comforts that I had, but you also realized how much, at least I did, in my daily life, how much time I spend and worry I spend on things that are irrelevant. And when I released that, I got so insanely creative

and had so much energy because like thoughts worry all that's it's exhausting i remember when i came home i said to my wife um we were doing carpool with our kids and she was going to take uh you know with two cars and she's like i think i'm like cool and then she came right and she said i'm going to take the silver car i'm like okay sweetie take the silver car and then she came back 30 seconds later she's like you know what i want to be able to park it i'm going to take the blue car i'm like great take the blue car and then i was I was like, do you know how much energy you just use on something that's like, but it happens all day long? And you don't even realize how much energy you use on like, at the monastery, all the decisions are taken away.

So what you eat, you eat whatever they give you. What you wear? Nobody can't. I changed once. It took one shower. It just was super freeing. So I left there incredibly energized. And I surrendered a lot of things in my life that just I didn't realize, you know, are time zappers.

And that might sound. obvious, you know, like, oh, you went to a monastery and you realized, but it wasn't about meditation, it wasn't about really religion or spirituality. It was just about simplifying and prioritizing and realizing, like, what's, I already know what's important to me, but realizing, like, to eliminate some of the things that really aren't important to me and taking away those precious hours. But I was at a restaurant, and my wife was running late, I was with my trainer, a friend of mine, and they were putting me on the spot with this one, But there was a girl at the other table, attractive girl,

who I thought was kind of like looking over the table, she was kind of staring at me and it was a little uncomfortable. And I told my friend, like, you know, I think this girl's like checking me out, man. I don't know. I'm not sure, but like, will you look over there and see if she's looking at me? And he looked over and she's like, she's checking you out.

And, you know, we started laughing about it. And then she came over to me. It's a super attractive girl. And I thought she was going to say, like, can I join you or whatever? And she said, are you Sarah Blakely's husband? And he laughed and this and that. And I said, I am Sarah Blakely's husband. She said, I'm a huge fan of your wife, you know, like the whole thing was about Sarah.

And I thought the whole thing was about me. And I write about that in the book, you know. But that's what happened. And it was a funny moment, you know. But I was, I'm so proud of my wife. and I'm her biggest cheerleader. And that's part of my job as a husband is to support her through the ups

and there's been a knock on with a lot of ups but also plenty of downs. Being an entrepreneur and is lonely. You went through the journey, man. It's lonely. And nobody worries about it when you're the founder like you worry about it. And you can give out shares

and compensation of this and that. But, you know, it's Tom's bar, man. You know? And so there's, times where you have to be super supportive and understanding. And being an entrepreneur, I'm very aware of that. So I think it's a good fit. So another thing you talked about in the book was that you actually, in the early days of your marriage, you guys would argue a lot because Sarah would ask you, you know, what are you feeling? And you say, I don't know. And she finally had this epiphany

where it's like, he really doesn't know what he's feeling. And what has it been like for you to learn to really be introspective and to understand your feelings. Because at least from the outside, and especially having read the book, it feels like you've gotten to a place where you're very in tune with yourself, with your intuition, which is another thing we should talk about. But what was that process like? Yeah, I mean, Sarah would ask me for years, she'd be like, you know, well, sweetie, how does that make you feel? And I would say, I don't know. And she would say, well, you know, something would happen, like a big event, like, well, what are you feeling? And I'd be like, I really don't know. And I'd be like, and I really don't know. And I really

really didn't know. And she would get angry at me. She'd be like, what do you mean you don't know? I'm like, I don't know. I'm like, you know, I don't know. What's going on in the Hawk game? You know, like, I would just deflect it. And she finally realized, like, I really don't know. And maybe that was a defense mechanism for me. I don't know. And I like to stay super happy, you know, and upbeat and blow away some emotions that maybe, but through this journey through the monastery and through Sarah's like really big into talking, emotions, playing, you know, we volley. She always says like she'll hit the ball and I won't hit it back. And, but now we're volleying a little bit more. And, but it's a work in progress

for me, you know, my form of communication has been running an hour or day. I've ran, in the last 25 years, I've ran 36,000 miles. You know, I've ran, what, 10,000 hours or something, you know, alone, basically alone. And that's been my meditation. And that's been my release. And that's been my emotional, you know, it's been my creative process. It's been my physical well-being.

It's been my, you know, my own form of meditation. And it's been my release. And that's it. I'm good. She doesn't do that. So, you know, I've had to work through some of that. The book was really fun in, And for anybody that's ever thought, oh, I must just be bad at meditation, the part where you

try to meditate when you first got there and you're like, I've got my transcendental meditation, I've been given my word, I can't reveal what my word is, but it sounds like a sushi restaurant. And I really wish I had some sushi right now. And I thought that was fantastic for people that think there's like some big mystical moment. If I remember right, you were like, I was waiting for somebody to say, let there be light. Yeah. And so if that moment never comes, what is it that does come from being by yourself? for that long. Well, just to play into that story, when I first got to the monastery, I went

into a room that was the size of where we are, and I had a bed and a light and a desk. And Brother Christopher was like, you know, my go-to monk in the experience said to me, we don't want to start tomorrow at 7 a.m., we will start with prayer, reflection, and meditation. And I was like, great. It's 6.50 p.m. What do I do for the next 12 hours? And he said, think. So I said, okay, you know, I just got there. I said, let me try to meditate. So I had taken a transcendental meditation crash course years ago and had a mantra. So I set my timer for 20 minutes as instructed and closed my eyes and, you know, immediately got bombarded with all the thoughts that would, you know, how are my kids, what's going on at work, all this stuff. And I was like, why hasn't the timer

dinged? I've been here forever. Let me. check and see if I actually said it. And I know that would be cheating. So I continued on with this bombardment of thoughts. And then after it felt like an hour, I'm like, this is crazy. I'll be here all night. Let me set the timer. And I went to set the timer and I looked at it. I'm like three minutes and 27 seconds. And I was like, I'm fucked. I'm here for 15 days, you know. And that was my first hour at the monastery. And I felt really alone. And, you know, like, I felt like I was on Gilligan's Island. And usually, like, you call your wife or you'd send an email. I couldn't do anything.

I just sit there and be like, fuck, you know. And I started calculating how many minutes I have left here. And it started really fucking with me. You know, I was like, what? And by day two or three, I was really flipped out. I was homesick. I was bored out of my ass. I was like, one of the lessons is going to hit me.

Like, just give me the cliff note version of this. But I realized, like anything else in life, There is no Cliff Note version. The only way for me to get this is to stick it out for the entire 15 days. And until I made that mental, because in the back of my head, I was already convincing myself of outs.

Seven days is enough. Who's going to care if I live in my life for seven days or 15 days? The book's going to be the same, you know? And I was giving myself an out. Once I flipped it and made the commitment that like, no man, you're here. You're in this for the duration. I eased into it.

started appreciating the routines of the monks, what they were doing, the lessons became more vivid, and it became a picture for real life. Like, you don't cut corners, and you make a commitment, and you're going to have to tough it out. And the lessons are usually in the last,

you know, like most people do 95%, the same. But the last 5%, I'm sure you experienced it a quest at times, like it's where 99% of the people quit. But it's the 5% with the last 5% when you hit the wall

and you finish the marathon where the growth is, not the first 18 miles. So I realized, and once I made that shift, the whole experience changed for me. I thought a monastery would just be all prayer, reflection,

meditation, and a meal a day or something. But a huge part of it is manual labor because they have to keep the lights on. And the monastery that I went to, which was not Buddhist,

it was Russian Orthodox. They were the largest breeders of German Shepherds in this country. And I remember the first day I was, my job, the first day was to be a distractor. So they were training one of the dogs and I had to like run in front of the dog and, you know, try to like get him off of his game to simulate traffic in the city or distractions. And the goal is to have the dog be able to walk unblemished no matter what you throw at him. And I was going career. I was running at him.

I was like, you know, doing the far trick, all that stuff. And the dog didn't waver. It just walked from point A to point B. And one of the monks that was training the dog said to me, it's no different than life. You know, it's like giving me all this like, you know, wax on, wax off shit. But he was saying, you know,

you're going to get distracted from your goals. And all these things, arrows are going to come at you all the time. But the same way this dog goes from point A to point B, even if there's a pork chop there, whatever your goal is, you have to get there. Thank you for tuning in. Continue strengthening your mind

by listening to our other episodes.