How to STOP BEING REALISTIC and SHOOT FOR THE MOON | Jesse Itzler on Impact Theory | Transcription

Transcription for the video titled "How to STOP BEING REALISTIC and SHOOT FOR THE MOON | Jesse Itzler on Impact Theory".


Note: This transcription is split and grouped by topics and subtopics. You can navigate through the Table of Contents on the left. It's interactive. All paragraphs are timed to the original video. Click on the time (e.g., 01:53) to jump to the specific portion of the video.


Intro (00:00)

The people that you meet in your 20s rise up in their 30s and are in great positions of power in their 40s. You don't know when you're 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. Everybody, welcome to Impact Theory. Our goal with the show and company is to introduce you to the people and ideas that will help you actually execute on your dreams. All right, today's guest is a wildly successful entrepreneur with a net worth measured in the hundreds of millions of dollars, but trying to understand him by his financial success would be to entirely miss the mark. What makes him fascinating isn't just that he managed to turn a 900 on his SATs and no formal business training into a business empire that spans travel, food and beverage, music and even sports. It's that he has one of the most fascinating life resumes on the planet.

Jesse Itzler'S Journey And Insights

Jesse's LIfe Resume (01:01)

Here are just a few of his highlights. He's a former MTV rapper who used to be label mates with 80s hip hop icons, Tone Lok and Young MC, and despite being white, he convinced said record label to listen to his demo by first pretending to be a well-known black rapper. He co-founded and built the world's largest private jet card company, Marquis Jet, with no previous experience in aviation, and when he launched it, he got sales by hoarding muffins. I'm not kidding. He's rented an entire mountain, hired a Navy Seal to toughen him up, turned his failed career as a rapper into a successful company writing theme songs for sports franchises, and now he's actually a co-owner of an NBA franchise himself. He helped launch the coconut water craze with Zika, which later he sold the Coca-Cola, and he's run 100 miles in a single day. He's also climbed the vertical equivalent of Mount Everest over a weekend and actually summited the most deadly mountain in the US, Mount Washington. In short, this guy does not take the easy road anywhere, and he's proven that fearlessness and tenacity count for a lot more than experience or family money. So please, help me in welcoming the New York Times best-selling author of Living with a Seal, the man who introduced the world to the legendary David Goggins, the author of the upcoming Living with Monks, Jesse Itzler.

Intro to Living with Monks Author, Jesse Itzler (02:12)

Thank you. My pleasure. That was an amazing intro. Your life is crazy. Absolutely crazy. In this whole concept of the life resume, you really sucked me in, and I had written an original draft of the intro where it was my more typical "what he does this and then this and then this." And I thought, "That's really to miss the point." And so let me start over and really look at it from that resume perspective. And the crazy, like broad stuff that you've done, almost always with no experience is really pretty incredible. When did you start thinking about that? Well, I realized 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. And I had no connections. My dad on 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 do it. 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 typing our 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, 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 Vinyl to listen to your demo. Sure. So the Marquis Jet story, 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 Oz where everything goes from black and white to color. People fly like this. This is unbelievable. I want to fly like this. And by the time we landed, we're like, "Let's start a private jet company." So we could fly privately, except we had no airplanes.

Jesse and a Partner on a Flight That Changed Their Lives (04:35)

So we went to a company called NetJet, 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 cart, which was called Marquis Jet.

How Jesse Landed the Meeting That Changed His Life (04:50)

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 NetJet's that owned all these airplanes.

Michael's Determination and Passion Story (05:41)

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 sing his daughter sang at the Aguilera concert, and that's how we got the meeting."

Once Jesse Landed Net Jets Interview, He Got Kicked Out and Had to... (05:51)

Well. But the meeting actually, when we pitched the idea, the meeting lasted 12 minutes and they threw us out. The president of NetJet said, and this is almost a direct quote, 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 taught me to piss me off, I got like a 980, but I've convinced myself, I've gotten over here, like, "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 mark it onto their fleet through this 25-hour program called MarquisJet, that's how we would piggyback out 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, you see, 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 guy stood up.

Jesse's Dedication Pays Off, Thanks to TED Losers! (06:46)

We had Carl Banks from the New York Giants and run from Run DMC in a powerful real estate mogul, and they explained that they would never buy a fraction of what NetJet was selling, but they would buy a 25-hour card if it was 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 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 to 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.

The BEST Way to Stay Focused on the End Game? (07:43)

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 five 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 was 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, "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. Look, I happen to have an extra muffin." Actually, I have 800 of them. But if you want a muffin, you can have one of my muffins. It's like, "No, get out of here." So, I said, "Oh, I said, "Well, what are you doing here?" We started having a conversation and he said, "Do you mind if I join you?" And I said, "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 99.9999% 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 the 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.

Writing the script (10:00)

I just had to write the script. And the script might change. There might be, you know, call an audible and you 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're not like a crazy endurance runner. Well, then let's think backwards of how, you know, 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, you know, 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 taking risks, comfortable with being embarrassed. And I think it comes from having a lot of egg on your face and learning along the way. You've talked about, I like to get my foot in the door and then I'll figure out the rest later. How have you not let, I don't know what I'm doing stop you? It takes a long time. You know, it's a fast world. It's a, to build into that learning curve. For me, 980, it takes a lot of time. I just never had that time. So 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. So let's talk about then the networking that you've done because the amount of places you've been able to get your foot in the door are pretty impressive. Have you done things strategically knowing like, this is going to help me meet people that could potentially one day open a door for me somewhere? Yeah, I mean, 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, time you've had some amazing guests I 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 mail. That's a lot different than it can 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, cab drive. It could be anyone. I would just get their card and I would thank them. That was my form of networking. Even to this day, I have a hot 50 list that I have 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. They always comment on it. Thank you so much. It's authentic. I'm not just writing it to write it. They have to really have had an impact on me. It's a meaningful note. It makes me feel great. And it makes the recipient feel attached to me in a different way. At an early age, I understood the importance of that. The people that you meet in your 20s rise up in their 30s and are in great positions of power in their 40s. You don't know when you're in your 20s, who's going to make it and who's not. So you treat everybody properly and respectfully and you stay in touch. And very often those relationships merge their heads years later, decades later. Well, it's really incredible. One thing that I find really fascinating and super effective about your personality is you'll capitalize and move quickly on serendipity. So this audience knows David Goggins very well. It was a phenomenal guest on the show. But what I love in your story is you see him running next to you. You see that moment that's really become a core part of his story where he's got the broken feet, but he still runs the remaining 30 miles. But you reach out to him afterwards and actually make something of that. What was that process like for you and why is that a thing for you to really, you see something you move on it?

David Goggins (14:34)

Yeah, I think well with Goggins, this was his first 100-mileer. And I was doing it as a relay race. So I was doing it with five friends. He had no one to really with. Like he was his only friend at the race and he was his own team. And immediately I was drawn to him because he was a super, he was a heavy set 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? 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 over did our supplies. I had a masseuse and a whole food truck pulled up. And like Goggins had a glass of water, a box of crackers and like a chair. At mile 70 he had crushed his feet. He broke several bones. And I 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 got to meet this guy because and nope at this time he was relatively unknown. And 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 blunning. If I could teach that to my kids or to my employees or to myself, like I want that secret sauce. And initially I went out because I saw a lot of star power in him. I saw just a whole different world. We represented something I 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 I asked him to come with me. And basically he said if you're crazy enough to ask a guy like me to come. I'm like mother fucker 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? You'll see something be curious, be interested and do more than just 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. I learned 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. And that is I'm on a constant search for that. Because I'm very aware of my own mortality. 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 you had on your wrist or something like that. I stopped doing that. Why'd you stop? I'm curious. I'm just so aware of it now. You know, it was started 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?

Relationships with money and time (18:02)

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 summers 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, 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 even going to be here in 100 years? So why would 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 hits the pillow where I don't say to myself, like, you know, did I maximize the day and am I, you know, am I aware of it? And, you know, am I aware of my mortality? And it might sound depressing, but it's not. For me, it's thrilling. It's thrilling. That does not sound depressing to me at all. I think I'm utterly fascinated by people that are really trying to get the most out of their life humanly possible. And knowing that you're one of those people, the obvious question to me becomes why are you so obsessed with doing the hard things? Like, if you know you only have 28 summers, as you said, why are we doing polar plunges, running 100 miles? Like, what is it about that drive to encounter not only the novel, but the incredibly difficult? 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, if not more important, to build your life resume because that's really an indication of what's going on. It'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. How does your obsession with time and, I guess, anything else that led you to do what you did with the monks?

Living with the monks (20:07)

So, what did you do? What drove you to do at what were some key takeaways? 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. You know, I didn'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 said so much energy because, like, thoughts, worry, all that's exhausting. I don't know when I came home. I said to my wife, we were doing carpool with our kids and she was going to take two cars and she was like, I think I'm going to take the blue car. I'm like, cool. And then she came right and 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 like, do you know how much energy you just use on something that's like, but it happens all day long. 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. That's a 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. What I found really interesting about the book and by the way, the structure of the book is phenomenal. The way that you invite us in to you having trouble writing the book and that we're experiencing with you, the meeting where you have to explain. I haven't written the book and it's supposed to be done. And then as you're reading it, you're like, wait, I'm actually already in the book. So it was like this sort of adaptation, if you ever saw that movie. It was really, really interesting. And I'll just assume this was intentional, but the very structure of the book had that same sense of dropping inside. So dropping inside of your mind that I imagine is exactly what happens when you go to a monastery and there are no distractions and suddenly it becomes about what I'm learning about myself. And I could, I don't think you ever actually said it in the book, if I remember right, but the sense was that the struggle in writing the book came from, I was looking for the universals that were so present in living with a seal and I found only myself in that.

Life Lessons And Personal Experiences

An Incredible Story about Marriage and Partnership (23:17)

And so how do I pull forth the the universals by telling these incredible stories. And that was really, really cool. And one of my favorite stories was Mr. Sarah Blakely. And it's just a really cool story. Walk people through that because it got to the heart of something that I think a lot of people struggle with. And your ability to both be the top dog in a scenario and to be a cheerleader is pretty remarkable. So tell that story if you don't mind. I will, I mean, to that point, I'll get to the end first, it's a key component of marriage is sharing in each other's successes and rooting for each other. And when the star shines on someone, you celebrate it and then the other person, you know, your partner celebrates it and being on the same page. And for a guy, that could be difficult if you're married to a gal that's in, you know, that has a light shining on them. 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, a attractive girl, who I thought was kind of like looking over the table. Kind of staring at me and it was a little uncomfortable. And I told my friend, like, you know, I think this girl is like checking me out. And I don't think, 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, you know, he laughed and this and that. And I said, I am Sarah Blakely's husband. And 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, you know, 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 a little, you know, not going to want a lot of ups, but also plenty of downs. You know, being an entrepreneur is lonely, you know. 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 are 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.

Why Entrepreneurs Can't Process Emotions Properly (26:14)

Because Sarah would ask you, you know, what are you feeling? And you'd 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 like, what was that process like?

Ian's meditation experience (26:40)

Yeah, I mean, Sarah would ask me for years. She'd be like, you know, "Sweetie, how does that make you feel?" And I would say, "I don't know." And she'd say, "Well, you know, something would happen like a big event where she'd be like, "Well, what are you feeling?" And I'd be like, "I really don't know." You know, like, and I 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 hot 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." But now we're volleying a little bit more. But it's a work in progress for me, you know. My form of communication has been running an hour a 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. 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, "You know, 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 use. If I remember right, you were like, "I was waiting for somebody to say let there be light."

How Ian experienced being at the monastery (28:42)

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, "You know, we'll 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 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 set 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 you like, you call your wife or you 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, "When are the lessons going to hit me? 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 on my day 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 like made the commitment that like, "No man, you're here. You're in this for the duration." I eased into it and I started like 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 this is where 99% of the people quit. But it's the 5% with the extra 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. You said being around a master of a craft is always enlightening and the monks there were master dog trainers. They were. Very surprising. What were your takeaways from that? 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, it 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 try to like get them 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 crazy. 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 are 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 got to get there. Even though people are going to say you can't do it, even though people are going to throw different opportunities, you know, I'm sure your friends went out a million times to happy hour when you were to stay late. And I mean, I was in the same situation. Those are the distractions that come at you. But to get to your goal, you can't go to happy hour every night. You have to return emails and you have to check the manufacturer and you have to check the inventory and you have to big sales calls. So I was getting these lessons, but being around the best at what they do, it was just impossible to not have an appreciation and respect. That's really interesting. And I think that a lot of times humans respond the same way when you meet somebody that's really just centered for lack of a better word. They're not being distracted. They know what they want. They're going after it. There's just an ease of calmness about them, which is really infectious. I'm drawn to it.

How How Have You Stayed the Course (34:17)

Yeah. So going back to the arrows that you were talking about, how in your life have you stayed the course? How have you stayed focused when you had and maybe this goes to your why? What was it that allowed you to keep going when your friends were going out to happy hour? Well, I think like everybody, I feel overwhelmed a lot still. Even though I'm older now and I've had some success and failure, but I still have a lot of arrows that come at me all the time. Requests for my time, challenges at work, challenges raising kids, being in a marriage is not easy. We have a great marriage, but it's not easy to work. And it's overwhelming. So for me, I think part of it is always having something big on my calendar that I can look forward to. Every other month, I try to put something on my calendar for a weekend that I can really look forward to. So it helps me get through the tough times. And I like to have one, at least one really big challenge a year that kind of centers me and keeps me honest. Keeps me honest. And that's really helpful for me. And then the other thing that I do that really helps is I have a journal and I just take everything that's on my head and I keep it in a master journal. It doesn't mean I'm going to get to it. It doesn't mean it goes away, but it gets out of my head and it goes somewhere else. The free up space in my head. And then I'll just work it off or I'll prioritize it from the master list, but just the act of taking all the stuff that's in your head, putting it on paper in one place where it lives, is like really freeing and energizing.

Did You Find Your Why (36:01)

So you talked a lot in the book about finding your why. Did you find a why? My family is so important to me. I have four kids under eight. So my why stares at me in the face every day. But for me, going back to what you said at the opening of the show, and we touched upon it, it's my life resume. You know, it's helping people is important to me. You know, I feel great being able to help people in any way. I love people. So I like that's a big part of my life. But my own personal resume is sort of my why. I just said to my wife as I turned 50, like, let's have a big, I don't have a big celebration. This is a monumental birthday and it's really affecting me, how I think. You know, it's like, I didn't think it would, but turning 50 is having a big impact on me. And I said when I was 25, I had a big party in New York City where I was living. I don't want to kind of replicate that. And she said, wow, honey, you know, think about all the things that you've accomplished in the last 25 years. And I'm like, I appreciate it. But compared to, I haven't done anything compared to what I, the potential and what I want to do, you know. And she said, well, then think about the things that you love to do over the last 25 years. What are the things that you love to do and who have you loved to do them with? And for me, it's been the races, the travel, the this and the that, civil look. Put as much of that on your plate as you can with the people that you love to do it with in the next 25 years of your life. And that's sort of my mission statement. So how is turning 50 affecting the way that you think I'm super curious? It just realizing that like it went so fast and realizing that there's so much that I want to do and being aware that your 70s are different decade than your 40s and 50s. Then you have 20 years left. And when you put it in perspective of how many weekends there are, you know, there's only 52 weekends and you start to look at it like that. You're like, I'm going to be 80 and 30 years scary. You know, I got kids. It's scary because there's a lot I want to do. I feel like I haven't done anything compared to what I want to do and the opportunities. So, you know, it just, how do you manage your time? I never thought like that. I'm thought I'm going to live forever.

Thoughts On Dreams, Risks And Time Management

How Do You Manage Your Time (38:23)

And, you know, I'm bulletproof and all that stuff and I'm not. And when you turn 50, shit happens. Friends get sick, you know. Let me give you an example of just how it's affected me and how even the monastery and this whole notion of time which we've been talking, it's been a theme of this conversation. But like, are your parents a lot? Yeah. How old are your parents? If you don't mind. 70. Okay. And where do they live? In different parts of Washington state. Okay. Did you see him? Yeah. Pretty often. Once to three times a year. Okay. So let's say they live to be 78, which is the, I hope they don't. But let's say that they live to the average age. So you see him one, you said once to three times. Yeah. Okay. No, you don't. That means you're going to see him 16. If you see him twice a year, you can see him 16 more times. When you look at it that way, you're like, what? You don't have eight years with them. You have 16 times with them. And that's the shift in my life. And that's the way I look at things. That's a fundamental shift in the way that I looked at situations six months ago.

How Can People Manifest a Dream (39:30)

And it's created urgency. It's created a need to just like not put stuff off and to recognize like what's on your list of things that you want to do. Yeah, man. That's really interesting. And the concept of urgency to me has been one of the driving forces in my life is the ability to create urgency even when it wasn't age. And I felt like I was going to live forever. That was still a huge driver for me. I need to do this right now. And that's been one of the things that's really served me as an entrepreneur. What advice do you have for the young upstart, whether they're young in age or just new in terms of going after something for the first time? What advice do you have for them like urgency to actually help them get across the finish line and manifest their dreams, not just a dream, but really make them come true? I think the first thing is like any goal is attaching yourself to something that you love to do. And we've heard that many times, but we often neglect it because there's an opportunity. Maybe there's more money. But like it takes a long time to build a brand or accumulate wealth or we hear of these get rich quick things and they happen, but they're not the norm. It takes time. So if you're not doing something over that time and all of a sudden you lost your 20s and your 30s, you never get them back. So I think the first step is to attach yourself to the passion that you like. I think if you're an entrepreneur, you have to understand the passion is around the process as well as the product and what you're doing. People often neglect the process, but you can't shortcut it.

Risk & Taking Chances (41:12)

And if that's what you're signed up for, you have to respect it. What do you think about risk and taking real chances? I'm a big risk taker in general, but not a thrill seeker. So I'm an adrenaline guy, I'm an endurance guy, but I don't go on roller coasters. I don't like I'm not jumping out of airplanes, but the bigger the risk, the bigger the reward. It's really interesting man and your life has certainly proved that there are some big rewards for taking risks. Alright, before I ask my last question, tell these guys where they can find you online. So on Instagram and all the social media.

The Impact He Wants To Give To The World (41:53)

Cool. And final question, what's the impact that you want to have on the world? I just, I mean it's person to person. It's person to person. You know, the world gets small. It's a big world, but our worlds are small. You're going to leave all this and you go to a very small world as do I. So I want to just positively impact the people that are close to me in a way that will carry on, you know, for as long as it can. Jesse, thank you so much for being on the show. Thank you so much. Alright, guys, this whole notion of a life resume has absolutely captured me. It's really, really fascinating. In his new book, Living with Monks, you are going to love it. Literally you feel like you're tumbling down inside his mind. If you've ever seen the movie adaptation, that is exactly what this feels like. It opens with him confessing to his literary agent that he hasn't written the book, that he was supposed to be done with by now. And then confessing that he kept a journal and then you sort of tumble headlong into the journal with the person that his agent. And then the stories that he shares and the exploration that he's going on, I mean, it's just really this fascinating look at one single individual's reaction to having their world shut down from a distraction standpoint. And the book itself becomes this like meditative practice in and of itself in that you see the universals. You see yourself in him as he's going through this. And it is really incredible. He has such a unique way of experiencing something and bringing it back to people in a way that's useful. And it's even self-reflexive in the book. How he talks about that, how there's so many things that you can't learn just from reading that ultimately they have to go out and experience it. And the punchline of the book in the end is he said he wants everyone to build a life resume, to go to the website and to pledge what it is you're going to do and then actually take action, which is why I was so excited to get him on the show. You guys know my absolute obsession is actually getting people to go out and act to do something. What this man has done with his life is beyond astonishing. Every time he hits a note to find some amazing, creative, hilarious and ultimately effective way to get to the other side. It is something that I hope you guys all hear in his story. This is not a tale of somebody who leveraged family money to make it even bigger. This is somebody who started with nothing and built an absolutely massive empire, not once, not twice, three and four and five times. It is absolutely astonishing. It's repeatable. It's something you can learn from. So dive into his world. Alright, if you haven't already be sure to subscribe. And until next time my friends, be legendary. Take care.



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