#14: Building Up Your Life Resume with Jesse Itzler

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When you join me here, we are going to chase down our goals, overcome adversity, and set you up for a better tomorrow. Come on this journey with me. Hi, and welcome back to Creating Confidence. I'm so grateful that you're here and that you're with me this week. Week. I am freaking out about this episode and about the story behind the story that I need to share with you. So hang with me for a minute while I give you the backstory. So this whole thing started about a year ago. I've mentioned before, a really good friend of mine, Scott McGregor, had reached out to me and I had just launched my book Creating Confidence, and it had just dropped, and I was all over the country promoting it, really working hard, getting the word out about my book. And Scott reached out to me during that time and said, I need a favor. I need you to write, be a contributing author, along with a number of other contributing authors in my new book, Standing O, which is all about gratitude and how you're grateful for someone in your life, how they affected you in a positive way. And I thought, oh, my gosh, I have no time. I don't want to take on another endeavor, another book to promote, blah, blah, blah, whatever excuses I was coming up with in my head. But I just knew one thing. This guy always posts for me. Whenever I ask for anything or help with anything, he jumps right in. So I had to jump right in. It's the right thing to do. So I was happy to do it. I wrote a chapter for the book Standing O, which is an amazing book, all for charity. I mean, how can you not want to be a part of something so good like that? So I became really good friends with Scott over the past year. Now, back then, I hadn't known him that long, and we really started developing our friendship through the book Standing O and through supporting one another. So during this time, he's been on this journey with me, you know, as an entrepreneur, as a speaker, and now as a podcast host and as an author. He's really been there every step of the way, always trying to help me out, always trying to connect me to people that might be able to assist me or work or help increase my network. And he's been such an amazing ally and advocate and friend to me. So this backstory goes back to him. When I launched my podcast, he was one of the first people to call me again and send me a note saying how proud he is of me. He's such. Oh, my gosh, such a great ride or die friend. So, anyways, he reaches out to me when I launched this show, and he said, hey, we need to get you some really major guests. Let's brainstorm right now, Heather, on who would those people be? You know, what does that great guest look like for you? So we started talking and sharing that I, you know, I wanted to showcase people who had reached massive amounts of success, overcome adversity, you know, really done the work. And immediately he said, heather, we need to get Jesse Itzler on your show. And I thought, yeah, that would be amazing. However, this guy is on massive shows, and my show is still relatively new. I don't know, do you think that we could get, you know, get him on? He said, I'm not sure. However, I am, you know, he knows Jesse. And he said, I know Jesse. However, I'm really good friends with his business partner. Why don't I connect you to him? And I can't promise anything, but let's start, you know, the ball rolling and see what happens. And in any situation, no matter what you're doing, you've got to. You've got to lay the groundwork. You've got to take those steps in order to get things going. Who knows if it'll take a week, a month, a year, two years, but you've got to start that process. So I said, great. He gave me his number, sent an introduction for me, and I got on the phone with Jesse's business partner, and we hit it off. He's a great guy, and we got along really well. I was trying to help him with a couple of different connections, and in the end, I said, is there any chance that you think you could help get Jesse on my show? And he said, oh, gosh, Heather, we're really trying to cut back on podcasts because he was doing a number of them for a while, and it just took up a lot of time. Of course, the guy's really busy. And he said, so I don't know. I said, okay, totally get it. Completely understand. I had to ask. However, you know, in the future, if there's an opportunity, just know in the back of your mind, I'd love to have him on my show. He'd bring a lot of value to my listeners, and I think I could bring him some value through promoting him on LinkedIn, you know, trying to add value and talk about how it could be, you know, mutually beneficial. And of course, I said, and I'm happy to go to him anytime. Because, as you know, I just so believe in the importance of face to face and being with people, you know, live in real time. And so his partner said, okay, got you. I hear you. You know, if there's an opportunity, we'll definitely keep it in mind. So a couple days pass, and all of a sudden, I get an email from his business partner connecting me to Jesse's assistant. And out of the blue, and it just said, hey, let's get Heather's podcast scheduled ASAP if possible, if Jesse has an opening in the next, you know, couple of months. So I was so excited, and his assistant was so nice to me and just such a sweet person. So she and I were back and forth trying to figure out, you know, how could we make this work? And I was really, you know, imposing upon, no, I'll come to Atlanta. Oh, no problem. I'll come there. I'll come there. And I kept getting kind of blown off about that. So finally, in the end, I said, okay, whatever, you know, if the best is that we can do is a Zoom interview, let's do it, because I still want to bring the value, and we'll just move forward with that. I was a little bummed out. However, you know, life goes on. So it comes the day that I have this. The podcast is scheduled for Jesse. I'm on the Zoom with his assistant first, because she wanted to test the computer out and make sure everything was all set for him before he came on. And it wasn't working. And so the Zoom kept going out, and I. I let her know. I said, listen, I just did a Zoom podcast yesterday, and I didn't have any problems with this. I think it's on your end. And she agreed. She said, listen, we're having some major Internet problems. I don't know. Let me go into another room. Let me go outside. So then Jesse gets on and was super nice and said, hey, you know, we're trying to figure out a way to make this work. Let me go to another area of the house. Let me to this area outside. So there was this whole back and forth of trying to get the Zoom to work. In the end, it just wouldn't work. It kept cutting out. So that's when I said, listen, one of my best friends in the world lives in Atlanta. It's such a short plane ride for me from Miami. Why don't I just come up there this week and we can just knock it out. It's 45 minutes. And so he said, yes. And that was it. Ended up being Just the greatest opportunity for me to get the chance to meet him face to face, meet his assistant and. And get to know him. So I flew out to Atlanta and I was so excited because I get to be with one of my best friends and stay with her and her husband and their family, and I hadn't seen them in months. So it ended up being this really amazing opportunity and such a meaningful trip for me. So I go out there and of course, I'm keeping my friend Scott updated with what's going on the whole time. So during this time, I said, scott, who else do I know that knows Jesse? Because while I was doing research on him, as I research anyone I'm going to interview, I wanted to find out, is there any other point of contact that I might have? And he said, oh, yeah, Heather, you know, his trainer from social media. You guys are connected on social media. So I messaged his trainer and said, you know, I wanted to get him in the loop and see, do you have any questions you think I should ask Jesse? So I was really trying to understand as much as I could about Jesse before I went to interview him and talk to everybody that he knows that's meaningful and important in his life that I might know. So I take these steps. I go to my good friend's house. We have a great time there, and the next day I'm going to interview Jesse. And I was really excited. I was very prepared. And I get to his house, and I will tell you, I have, over the course of my career, in my lifetime, I have known a few different billionaires. And in my mind, that stereotype or the experiences I've had with people with that amount of wealth is sort of. I see it one way now. When I got to his house, I was really surprised. Other than, you know, obviously there was tremendous security and, you know, that part's, you know, a little different versus what I'm used to. But once you walk in the door, it was like walking into your own home. Super comfortable, pictures of the kids, you know, really normal is the best word that I can think of. And it was. It made me feel so relaxed and at home, and everyone there was so nice and so accommodating and really just. It was an amazing experience. So I was brought down into a room to wait for Jesse. He was on a call or in a meeting, and I was sitting in this room waiting. So I am a little bit curious. So I start looking around and I see there was a magazine cover or book. I don't remember exactly what it Was. Was Sarah Blakely, the founder of Spanx, Jesse's wife, on the COVID And so I pick it up and I'm so excited looking at it. And I think, oh my gosh, I should totally take a selfie holding this book standing in front of their bar, you know, and I'm put that on Instagram. And as I'm about to stand up and do it, I think, oh, my gosh, you knucklehead, this is probably not the best idea if you ever want to be invited back here again. I bet there's probably cameras. So luckily, now that I'm in my 40s, I have a little bit more wisdom than when I was in my 20s. I start to look around, I see a camera and I say, okay, all right, Skippy, dial it down a little bit. And you know, put the book down, sit back down.

Okay.

So I get myself back together and I am just looking through my notes or whatever and in walks Jesse. And he couldn't have been nicer. Amazing energy, you know, just such a great guy.

And.

And the best part about this was he brings me into his office where we could record, and I pull out my. I have a traveling microphone so that I'm able to interview people on the road and be able to go to their homes and interview them when, you know, we can't do it in studio. And I pull out my microphone. He says, oh, you're packing props. And I said, no, I'm not packing props. This is legit how we're going to do the show. And he was really blown away by that, so I thought that was kind of funny. I pull everything out, I'm getting organized because I wanted to be respectful of his time and I did not want to go over. And he said, hey, hang on a second. Tell me about you, Heather. I want to hear your story first before we start talking about me and go on your show. And I thought that was so nice. You know, so many people are rushed in their day and are in back to back meetings, which he definitely is. However, it was really thoughtful and just really sweet that he wanted to learn about me and hear about what I'm dealing with in my life. And it was so cool. I end up telling him about my son and how he had that awful experience at sleepaway camp. And I was nervous because he was actually at the Duke camp right then. And then it was so ironic. Jesse tells me, oh my gosh, I went to the men's basketball sleepaway camp at Duke and I know Coach K and he's my friend, your son's gonna have the most amazing experience. And then he opened my eyes to something really cool. He said, heather, the fact that he had this negative experience is good. That is a character building moment. Life is not easy. And he said, I really celebrate those challenges that my kids have and face because then they can see they were, they were able to overcome that. They were able to overcome that adversity and bounce back. And he explained to me that it was probably a really great thing that Dylan had a negative sleep away experience because now he was in this amazing experience. And it would open his eyes to the fact that just because you have one difficulty or challenge doesn't dictate the rest of your experiences. It just shows you that you can grow from it, overcome it, and then have great experiences moving on. So I was so happy to hear that. It really made me feel so much better. And in the end, he was so right. My son loved Duke Sleepaway Camp. Already signed up for next year, wants to go the whole time. And it ended up being this great bounce back story for a 12 year old. So that was so cool and made me feel so much better. Now all this goes on. We have a great interview. You're about to hear it. And it was just such a great experience. I had to jet out of there because I promised my girlfriend I would babysit her little son so she could go to a meeting. So I had to run off. But Jesse was so nice and I said, you know, would love to work together in the future. And he said, let's stay in touch and you know, keep me updated on your progress and your business. I'm behind you, I'm cheering you on. He was just such a great guy. So I leave there, I call Scott immediately. You know, I'm so grateful and thankful for him. We're talking and he says, you know what, Heather? You should be speaking at Hypergrowth Boston in September. I know Jesse speaking there. You know, you guys hit it off. You guys should work together again. He said, I'm gonna call the CEO and tell him that you need to be on that lineup. So yet again, my good friend makes a phone call for me and wouldn't you know, a week later I hear from the Hyper Growth Boston team and they were amazing. And they said, heather, we'd love to have you as a speaker at our event. Would you be able do it? You know, let's work out the logistics, let's set up a call. And I was so excited. And then I heard that they wanted me to Interview some people. And I. At first, you know, when you create an idea in your mind of what you want and how you want things to be, you can feel a little let down when it doesn't turn out that way. So at first, when I heard I got a message saying that they wanted me to interview someone instead of do my keynote, I was a little bummed out. However, you know, in the end, it ends up being this amazing opportunity, because what I found out is I'm interviewing Jesse and his wife, Sarah Blakely, which is such a cool thing, because now I have this friendship with Jesse. I haven't met his wife yet. I'm so excited and honored to get the opportunity to meet her. But to be able to work with both of them together is. I'm so looking forward to it. It's going to be amazing. And all this happened and started over a year ago with a good friend of mine reaching out to me, asking if I could help him with something. And I just think it's so important that we're grateful for the good people in our life, that we make time for them, and when they need us, we show up for them, because my good friend Scott shows up for me all the time. And in other serendipitous information, he actually reached out to me about a week or two ago and said, heather, we're coming out with our new book, Standing O. Encore Again. All for charity, he said. And I met with my team to figure out who was going to do the forward and who was going to do the quote for the book. We decided Jesse and asked Jesse Itzler if he would do the quote. He's agreed. But the team would love it if you would be willing to write the foreword. I had never written a foreword for a book before. I'm so honored and to be a part again of Standing. Oh, and this time, the encore. I am just. I was about to wrap Jay Z. I had to pull myself back. However, I'm so grateful. I am so appreciative, and it's just crazy how serendipitous this is all working out. And I truly believe that when you follow your passion, when you show up as your real, authentic self and shine your light, amazing things just start connecting and working out. And I feel like I'm really on the. I'm on the cusp of that right now. And it's such an amazing feeling. So I don't want to give you so much backstory because I just want to get to the interview because you're going to Flip out and love it. He's such an amazing extreme guy. Extreme is definitely the best word because when I first met him, he said to me, I'm so sore. I ran 40 miles yesterday. I about fell over. I don't even under. He's older than me. I don't even know how this man's knees hold up. But I will tell you, if you want to be driven or pushed, he is definitely the one to follow on social media and you're going to get that kick that you need to go to the next level. Surrounding yourself with people that are ahead of you is always such a great idea because it pushes you to realize how much more you can do, how much farther you can go and how much harder you need to try if you want to get to that same level of success. So as always, you know I have some deals for you guys and I really have an amazing deal right now. So please jump on this. This is not an ad hyper growth. I am getting an amazing opportunity to interview Sarah Blakely and Jesse Itzler. It is going to be unbelievable. I'm so excited and I want to see you in Boston. So September 3rd, you better meet me in Boston. These two tickets are expensive and for good reason. The lineup is insane. However, I have a code for you today and the code is Monahan, all caps. If you want a free ticket, these tickets are going for five and six hundred dollars. This event will sell out. It always does. You need to use my code Monahan to grab free tickets right now. September 3rd in Boston. 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Hi and welcome back. Thanks for joining us again. You are gonna flip when you meet this guest. All right, let me tell you about Jesse Itzler. He only eats fruit until noon and I will go ahead and say that's true. I'm seeing it happen. Loves Run DMC because he's tricky, tricky, tricky and enjoys living life out of the box. That's actually an understatement. He co founded Marquis Jet, the world's largest prepaid private jet card company, in 2001, which he and his partner sold to Berkshire Hathaway. That was not an easy meeting to get. He then partnered with Zico Coconut Water, which he then sold to Coca Cola in 2013. He is a former rapper. I mean, I can't even believe this. This is insane. He produced and SANG Both the NBA's Emmy Award winning I Love this Game music campaign and popular New York Knicks anthem. Go New York, go. What are you doing living in Atlanta? Itzler is also the author of Living With a Seal, New York Times bestseller number one la Times number one Amazon, that book crushed it. And Living with the Monks Again. Another crazy move when he's not out training for his next 100 mile run or yesterday 40 miles. Jesse can be found at the NBA's Atlanta Hawks game where he is an owner of the team. He's also married to Spanx founder Sarah Blakely and the couple and their children, their four children live in the atl. Jesse, thank you so much.

I love this. We're face to face.

I know. And we're only face to face because your Internet wasn't working.

I know. I love Face to face and I love that you took the initiative to be like, my Internet wasn't working. Like, I'm gonna come do this live.

Yeah. Because, you know, and one thing in researching you, you and I are very similar in that way. If an opportunity is present in the moment, it's key to convert because you never know what's going to happen a couple months later.

Right. Well, you took advantage of it and here we are. I'm super psyched to do this.

Oh, thank you. I'm so excited. So one of the things that I wanted to, I watched so many of your interviews and read so much of your material, done your course, you know, build your life resume, that concept, which is your online course. It's interesting. I grew up and lived the build your work resume, send out resumes. And I remember hearing that when you were leaving school and you weren't big into school, that wasn't, you know, your jam necessarily. All your friends were building their work resumes and sending out work resumes and you weren't. What were you thinking back at that time?

Well, I mean, I was always a go getter. So even when my friends in college were sending out resumes and obviously I had to get a job, I've always, you know, I've always really focused, always. Even when I had no money, I slept on 18 couches when I was coming up, trying to make it in the music business, etc. I always invested in experiences. I always felt like that was the best networking opportunity. It made me more interesting, it made me feel more alive. And even at a young age, like if there was an opportunity to go to a conference or to take a trip, I would like, I would figure out a way to make it happen. Whether I had a volunteer there, sneak in there, save money, put it on a credit card. I just always was really into experiences. And I just remember, it's funny you said this. When I was starting out, my dream was I'm gonna work mega hard to make enough money that I could take a two week vacation. Like if I can make a two week vacation, 50 weeks of work will be worth it for the two weeks that I can go to Hawaii and sit on the beach. And those goals started to change and two weeks became four weeks and four weeks became eight weeks. But no, I mean, I've worked really hard in my life to get to where I am, but I do believe in building your life resume. We focus on traditional resumes so much and they're important, but it's also important not to lose track of, you know, putting on experiences and living and doing what you love to do, especially when you get older.

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Friday one to remember living, yeah, living your passion and finding a purpose driven life is essential in living your best life in my opinion. However, for people who struggle with money and you, you had situations in your life where you did not have money. They don't think that's available to them. What's the advice or direction you give people in those situations?

I mean, most of the things that I've done in my life don't cost a lot of money. I mean it's an easy excuse to make and I'm sensitive to it obviously and I can afford to take a trip. But I just, I went camping in this winter with my son, my oldest son, outdoors at Mount Washington. We slept in the snow in a sleeping bag in minus 5 degree weather. It cost $18 to park. Now of course you need a sleeping bag, but it wasn't like, you know, luxurious. Right. But it's something that he'll always remember. We still talk about it. The experiences that I'm talking about are really more about just getting out of your routine. Most of us live our life in routine so we get super comfortable in our day to day stuff and life goes really fast. When you do that. You hear it all the time like oh my, we were just talking about your son. In six years he's going to be, it went like this, he's going to be in college in six years. When you get outside of your routine instead of maybe watching football every Saturday, once every month or two, all of a sudden you take your kids on a picnic. Whatever it is, it just changes the dynamic. And that's the kind of thing that for me has been like a tremendous gift to my kids, to myself. And I've had a really unorthodox business career A very unconventional journey. Happy to talk about it. But I think the number one thing that I would say I'm proud of is just like. Like, I've had amazing life experiences with amazing people and became really bonded through those experiences.

So where does that unconventional approach stem from? Because it truly goes back to the beginnings with you, from what I can see.

Yeah, I mean, I started out in the music business when I was in college. I grew up in New York in the 80s when hip hop and rap was coming on the scene. And when I went to college, I was really into it. I was like, I'm making a record, man. I'm making a record no matter what. And when all my friends were making resumes and sending out resumes, I was going to, like, open mic night. I was in the studio, and I didn't have a resume. I'm like, I'm gonna go figure out a way to get a record deal and. Because that's what I wanted to do.

And everyone was telling you no, obviously.

Everybody? Yeah, everybody.

There was no one white rapping?

No, not really.

This is pre Eminem days.

Pre Eminem, Pre vanilla.

I. Oh, my gosh, Pre third base.

I mean, I'm sure everybody was doing it in their own garage or whatever super early. And I just felt like that's what I wanted to do. I could always go back to school. I could always go get a job. But this is happening now, and I want to be, you know, and there was no b plan, and I got a tremendous amount of rejection. My dad owned the plumbing supply house in Minneola, Long Island. I didn't have any connections. And it like, the end of the movie was, I'm getting a record deal. And then I had to fill in the plot. And the script changed a lot. The plot changed, but that end of the movie was always, like, completely unwavering. And I figured out a way to get myself into a meeting where I kind of took the liberty to say I was somebody else. I don't know if I would do this at this time. As a black rapper, guy named Dana Danes. I knew the owner of the record company loved Dana Dane, and he thought he had a meeting with Dana. And I gave him, while we wait for Dana, can I play my demo? And he was like, sure. And I was like, great, because we're gonna be waiting here forever for Dana. So I'm glad you said that. And I played my demo, and that led to getting signed. That's after a lot of rejection, a lot of no's, you know, a Lot of two years of just having partners that quit because they couldn't go the whole district. Most people can go the same 95% of the journey. But the last 5%, when the shit really gets stinky, most people can't handle that. And for me, I wanted it so bad. It was in my DNA that. That last 5%, it was just a phase where I saw everybody get weeded out. And I was just kept going until I got this meeting and ultimately got the deal.

That's a good way to see it. That's the weed out phase. When you start seeing everyone hit the adversity and some people are just giving up, that's when a lot of people want to say, I should give up too. This doesn't make sense. Obviously everyone else is going that way, but in fact, that's the weed out moment. So that you survive.

Yeah, I mean, you mentioned this 40 miles I ran yesterday. I'm training for an ultra marathon. And, you know, I get energized. And this is probably not the right route for everybody, but there is energy when you see that you're stronger at a certain point than others. Like, it does give you, like, wow, this training did work. I do feel good. Like, it is reinvigorating. And again, I'm rooting for everybody. I'm not rooting for anyone to not do well at all. But when people start to drop because they can't do it, it's like, are you kidding me? It makes me even more fired up. Like, I don't want that to be me. Because when you quit, it's over. You're done. You're done. So that's never been my. It doesn't always work out. But, you know, I've always really wanted something. I really, really want something. And that want is bigger than the obstacles. I like my chances. If the obstacles are bigger than how badly I want it, they're gonna defeat me.

So you talk a lot about, you know, having that vision. Is that about manifesting for you? Is that about, you know, when you just see something, you create that vision. You focus on it. Is that manifestation for you.

I just go three years out, like I always say. Like, you know, I talk about this, my wife, a lot. Just, I always go to the future, like Marquis. I always go to the end right away in my head, what could this be? Can I do this?

What.

What would this look like? What does success look like? That's how I start the conversation. I don't start with, I'm scared. I don't have Experience, I don't know anybody I start with, what's the opportunity? Do I have a different take on it? Can I be disruptive? And I go to the end, how big can it be? I already ran the 100 miles. When I ran my hundred mile race, I had to fill in the blanks, but I already ran it in my head. I already had the victory party. The documentary was filmed, my parents were congratulating me, we were crying. It was super visual for me. And then I had to say, okay, now I got to go to work. I got to go to work to get there.

So the power of visualization is a key to your success.

It's one of many strategies that I use to help me. But yeah, I mean I could give a million examples of it. I just got involved with a gum company that I'm about to purchase and I went right to like, what could this be? Why I ask myself all the time, why are we different? How are we different? What makes us different different? And what could this be? And if I can check the box on, wow, we're uniquely positioned this because of this. We're going to be disruptive because we have this. So we're going to stand out and this is going to get sold to a major company because of this. And then, you know, whether or not I have the tools to get there is irrelevant to me. I don't know anything about the gum space. I know anything about music. I don't think about running. That's irrelevant to me. It's like, you know, I'll figure that out, I'll hire that. But is the end of the movie clear? And that's the starting point for everything.

So you bring up the white space, the unique value proposition which really for you in your, the way you story, which is so important in sales and marketing, it is about the brownie and I love that brownie story. Can you share that story?

Sure. I was just thinking like, I think I might have been married to my wife before I even met her.

In my head you were, I think.

I was fully in a full blown relationship. And then I just had to convince her no. I mean, I learned it at an early age. I was taking an advertising class my senior year of college and we had to create a fictitious brand from scratch. Billboards and packaging and slogans and all that stuff. So I had a roommate in college that had an aunt Franny and she just sent us send us shipments of brownies every month. And I don't know what she put in it. She was a Little hippy ish. But they made everybody happy. And I was like, I'm gonna market these brownies when I get out of college. I don't want to go work for anybody. I'm gonna just. I'll start a brownie company called Aunt Brandy's Brownies. So in this advertising class for our final, we had to create this whole campaign. I'm like, well, let me do the campaign. If I can learn from the class, I'll use them as my R and D department. And if they like the campaign, I'll just roll it out after college, and that'll be how I'm going to market this brownie company. And we got in. I got selected to pitch this campaign in front of the class. And 30 seconds into my presentation, the professor stopped me. My parents paid $160,000 for four years of tuition, like $40,000 a year to go to college or something. Or today, at least that's what it is today. I think this is the only lesson that I learned. And the professor stopped me in the middle of my pitch and he, he said to me, what's your point of differentiation? And I was like, what does that even mean? He said, how is your brownie different than all the other brownies on the market? Because if it's not, this doesn't really matter. There's a thousand brownies. And substitute it for a podcaster, author, restaurateur, whatever it is you do, there's a lot of those that come out every year. Your brownie, whatever your brownie is, has to be very different than. Than everybody else's. And from that moment on, as a 21 year old kid sitting in class, you know, I've always asked myself, well, what does make my product different? How is my book different? How is, you know, how do I treat my customers differently or retain them differently? If I have a podcast, how do I follow up with my audience? How do I make them feel really, you know, emotionally connected to me, et cetera? And I ask myself a lot of questions around that. And that's always been, you know, a driver for me.

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Yeah, I mean I try to do this, the blocking and tacking that everybody has to do. Right. My day starts the night before I map out what my day looks like. You can actually see it on my board right now. I map out where I am, so I'm not at a phase. None of us can afford to just wing it, wake up and be like, I don't know what is today. There's too much talent to just wing it. So I try to prepare the night before and I do all the blocking and tackling that everybody does that you have to do. I deal with the problems head on. But I think the one thing that I do is I layer on top of all the obvious stuff, the stuff that, like, a lot of people don't do. Let me give you an example. The other day, again, we were just talking. We probably should have rolled the tape earlier. We were talking about how your son's at Duke basketball camp.

Yes.

Coach K is the coach at Duke University has a basketball camp for guys 35 and older. And he's been doing it for 15 years. Yeah, I've been going since I'm 35. I've been going for basically all 15 years. And about three months ago, I landed in Carolina and I just said, oh, Carolina. My head went to Coach K and I sent him a text and I just said this. I said, coach, I just wanted to thank you for having this camp, you know, for those five days. It makes me feel like an eight year old. I'm reverse aging. And I know you don't have to do that, but it really had an impact in my life. You don't have to respond. Thank you. Now there's 500, maybe 1,000 people that have gone to that camp. Nobody texted them formally. They might send him a thank you note after the camp. Probably gets 100 of those, 200 of those. No one's texting them four or five months before the camp. Three things can happen. One, he might share that with his wife. Got this really cool text, and it was more emotional than I'm saying. I'm giving you the spirit of it. He might share it with his staff. But three, it's definitely going to stand out because it's like so out of the, like, thin air. When I go to camp in a month and there's 500 or 1,000 campers or whatever, who's going to get the first hug? I now have permission to go up to Coach K. If I see him in a restaurant, be like, coach, I sent you a text. I don't know if you got it. I have permission because I'm not. I don't want anything. It was like an authentic thing. Now, that text took me 45 seconds. If I invested three minutes a day, three minutes a day to send three of those to a supplier, to a customer, that's a thousand, more than a thousand texts that I'll send in a year for three minutes a day. That three minute investment will hit 1,000 people in a year. Now, if you do that with the blocking and tackling, with a handwritten letter, with all the other stuff that I do, I'm Talking about these 15 things that I do, and I do pretty much all of them, your chances go up. Lot greater than someone who's just cold calling or going, you know, whatever they're doing. I do everything. I do everything every day.

It sounds exhausting, though. So how do you not get burnt out?

It's not exhausting because it's like, I also say no to a lot of stuff. I focus on the things that move the needle in the most important buckets of my life. Like my customers, influence influencers. Part of being an entrepreneur is figuring out how to get from A to B the fastest. Coach K is the guy that can move the needle and get me from A to B the fastest on certain things. If I have a chewing gum and, you know, he tweets it or likes it, that's gonna reach a lot more people follow him than me. So I focus on the right things, and I say to no to things that. Like our time killers. And I get a lot of requests for my time, and I do, of course, say yes to things. But 15 minutes, because if someone wants to pick my brain four times a week is an hour a week. That's like. It adds up. So I really focus on. It's exhausting if you don't do it right, if you're organized and you do the important things. I've been taking three hours a day for myself since I'm 21 years old, and every day religiously. And that's cumulative. It could be an hour run in the morning, 15 minutes, I'm getting a massage, whatever it is. But I don't have any guilt that I'm not with my wife or my kids or working when I take that time, because it makes me better at work, it makes me better with my wife, makes me better, more present with my kids, makes me be where my feet are because I'm checking the box of the things that are important to me. And when you do that, the other shit's not exhausting because you've already taken the most important stuff, you've already put yourself first. And that's like an unwavering Characteristic about me. It has nothing to do with money. I did it when I was sleeping on couches.

How did you know to do that back then?

It made me feel good. It made me. I would go into work and I'd be like. I look at people like, oh, I had to do this commute and I got stuck. And they're like, I wish I could have ran today, but I didn't have the time. And I was like, people were miserable and I was like, I had nothing. I had $118 in my bank account and I was loving life. I was going to concerts that were free at Irving Plaza. I was running marathons that cost $65 to register for. I was fishing on the east river, you know, with a. Fishing, like, I was doing shit that billionaires were doing. And I had $118. And now I'm doing it. I'm just doing it bigger, you know, like, I don't have to sneak into this. I have my own swimming pool, but I'm still swimming. I was swimming back then. I was going under a fence, but I was still doing it.

That's amazing. It took me until my 40s to realize putting yourself first is not something to feel guilty for. So kudos for you getting that early on.

If you could free up, let's say I'm 50, let's say I live to 80. If I freed up three hours a day, every day, right. I would basically get four and a half bonus years of time. And that's 24 hour day bonus years. If you took out sleep eight hours a day, it's like six hours, six years of life. I have bonus years. I'm just like, I've figured out. I've invested a lot of time and resources to figure out how to optimize my life, you know, And I really, I don't have it all figured out, but, you know, I do prioritize myself, my family, the things I like to, to do. And I still work really hard and it works.

You work very, very hard. Clearly I have been able to get a glimpse of that. And that's hard. Nothing beats hard work at the end of the day. Wouldn't you agree with that?

Smart work, I think beats hard work.

Being more efficient. Sure, for sure. But you just still have to show up and do all. You know, it's the grind when I've looked and researched so much.

Can I interrupt for a second?

Yeah, sure.

I found that. And I'm not the smartest guy for sure ever in the room, but I realized That I could be one of the most interesting in the room. So through these experiences, taking my son camping, I can win. I can control the tone of the meeting in the first 10 seconds without anybody even knowing. If I walked into a meeting with somebody and I saw he had all these rock, you know, I don't know. He's gotten a lot of adventures or he's a runner or whatever. A lot of times in the offices, my office included. You're here now. You get an idea of what people are about. And if I. I'll just use adventure, but I could use business school or anything, actually. I'll keep it neutral. If I walked in and I said, oh, my gosh, I'm so glad my parents are elderly and they're staying at my house. Just last night, I was getting my dad ready and taking his pajamas off or whatever, and it's like, it's just exciting. I'm excited to be here because it's just breath of whatever. I've already said to them, I'm loyal. I'm a family man. My priorities are right. The meeting hasn't even started, and they've already realized, like, they can trust me. I'm loyal. I have my priorities right. So, like, working hard is important, but working smart and, you know, and experiences. If I said, I just use the example. I just took my kids. We got back from Mount Washington. My son was outside in the snow and just feels good to be in a warm office. I've already said so much. I've connected with that person. If that's something that they're aligned with through my experiences. Now he's interested in me selling. Whatever I'm selling is gravy because we've already connected, and that's always how I've operated. You were a rapper. You talked about that in the beginning. We could talk about that. It's going to be compelling. You ran 100 miles. We can talk about that. You take care of you. We could talk about that. You have kids. We can talk about all those things. And it's like, there's a high chance you're gonna. You're gonna want to talk to me at the lunch table or do a deal with me, as opposed to someone that, like, I went to business school. I learned a lot there. And then I was an accountant, and, like, that's important. But sometimes the other stuff is more important.

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Well, that's about connection. What you just described, through being authentic and through being yourself. When you're your real self and you show up, like you said, you pay attention, but you share your story in a real way with someone that draws people into you. A lot of people don't want to be vulnerable. The guy that's instead saying, hang on, let me tell you my work resume right now. I went to this school, and here was my gpa. That person's not going to connect at the same level.

No. There were a lot of months where I was the lead salesman at Marquis Jet, and I was probably the least about the airplanes. And the reason was is I would go in and if I saw a guy had a running watch on, I talk about running. And we would just talk, and we would get comfortable, and we'd have conversation. And, like, you know, like, I always say this. You're the business plan. You are the business plan. So if he got comfortable with me, then I could be like, look, if you want to fly on a private jet, I have this amazing company. I'm the co founder. I love to talk about it. You know, call me. No pressure. That was my sales tactic. And, like, it worked. And it wouldn't work for everybody, but it worked for me. And so going back to what we talked about at the beginning of our conversation, your life resume, it's important. And, you know, I just turned 50. The average American lives to be 78. So if I'm average, I have 27 summers left. I hope I'm not. I hope I have way more than that. But, like, when you start to think reverse engineer, what you have left, reverse engineer, like, okay, your son, hopefully he lives to be 120, and he's got, you know, 108 more years. But you only have six years left in the house. Like, you only have 300 weekends left with him in the house. He's gonna be away some of those weekends, and you'll be away some of those weekends. When you start to, like, really think about things instead of like, we're gonna live forever, you get urgency. It changes. And, like, I don't want to be 80 and look back and be like, I didn't take that trip. I didn't run that race. I didn't go to that CEO because of, you know, I was scared or what. I don't have that kind of regret. So I really, really, really, really prioritize that in my life. And I'VE been doing it since a young age.

So do you think your kids are seeing this with you and living like, how are they different growing up the way you grew up versus the way they're growing up? How can you project their future, or do you think about that?

Well, I have a couple of strategies that they're the beneficiary of. So one of them is, is I take one on one trips with my kids. My parents are amazing, but they didn't have the luxury of doing that. I take family trips. I mean, and what I do is I schedule that before the year. Before the year starts. I have a big calendar. I'll show it to you. And I reverse engineer the year. Instead of being, like, looking at the year and being like, you know, what are we gonna do here? What does the summer look like? I'm like, here's 10 things that I'm doing this year to make it a 10 out of 10 year, a rock star year. I'm running this race. I'm taking my kids to this ski resort, to this mountain. We're gonna go fishing. And I schedule it so they're the beneficiaries of those kind of experiences. And our parenting style is to emphasize effort, not the results. It's effort. And to allow our kids to experience disappointment. That's how we parent or try to. And the trips and the experiences. They're encouraged to do it because they see me doing it. They see me doing it all the time. Every eight weeks in my calendar, I take. I do something. I do some kind of trick, some experiential thing, and they're around that energy, so I hope it rubs off on them. I was just at a. Is my A.D.D. kicking in?

No.

Let me know. Tap me on the shoulder.

You're good.

I was just at a meeting with the financial planner. We were talking about being a different brown 50 financial planners have pitched me over the last five years. And basically, they come in with the same deck with a different corporate logo. Hey, I'm from this bank, I'm from this. And they go through the same kind of spiel about life planning or insurance and this and that. Like, I'm craving someone to walk in and give me a different perspective on this. Be like, listen, on top of this, I have a nutritionist and I have a vet. Just give me, like, a different thing to chew on. Anyway, someone came in and he opened the conference, the meeting, and he said, look, if you could leave your kids with a lot of money or a lot of life experiences, and you had to choose one. What would you choose? And of course, you choose life experiences so they know how to, you know, handle.

Sure.

So that's sort of what my kids are experiencing.

So, you know, one of those stories that I think is so interesting and to me describes your creativity, which I. On the outside thinking your creativity is a big part of your success. Would you agree with that?

Yes.

Your creative approach to different things. One of the stories I really liked that I heard was how you got your wife to go on a date with you.

Yeah.

Can you share that story?

Yeah. I mean, we. Sarah, my wife, was a customer of ours at Marquee Jet. We met at a customer appreciation poker tournament. We were only allowed to. Each rep was allowed to invite one person from their territory. So the Georgia rep sent a picture of Sarah. I'm like, she can come. Don't send any more applicants. Let her come in. And we were friendly. We became friendly. But you talk about the sauna.

No, I was talking about when you called the assistants and you would run the race.

Oh, yeah. So, I mean, there's again, like, the movie was already baked in my head, so I had a.

You knew it was happening plot, things.

That happened for me to, you know, out kick my coverage. But I was running this 100 mile run, and I was sort of friendly with Sarah at the time, but not. Not in a big way. And I just called up her assistant. I was like, look, Lisa, I'm Jesse Itzler Marquis. Sarah this and that. I said, I'm running this 100 mile run, and I'll run the whole race in Spanx, like, women's underwear for a testimonial from my website from Sarah. And she's like, what? She put me on hold. She's like, sarah, this nut job is on the phone saying he's gonna run 100 miles for, like, a testimonial or maybe a donation from Sarah. Sarah's like, I think I know this guy. And a year later, we were married.

I love that. But it's just that that is that quote, unquote, thinking out of the box that so many people struggle with. Do you intentionally find yourself saying, okay, how am I gonna come up with a creative approach to this? Is there a plan or strategy you have to do that or it just happens naturally for you?

I think I'm not. I'm really not scared to be bold, you know? And my brain is wired of, like, how do I get, like, this done? It's not wired. You know, this is how everybody else does it. It's Just, I remember when I was a kid, we went to the US Open. I grew up in New York in the summer. And we would go with no tickets. We would take the train to Shea. We walked to the US Open, and I was with my friend, like, we gotta figure out a way to sneak in so we can get into the US Opens. Like, we can't get in. We don't have a ticket. I'm like, of course we can get in. We figure out how to sneak in. Like, we don't need a ticket. And we figured it out. If we held onto the wire when the camera guys walked from the CVS truck into the thing, they would think we were interning and just walk right in. So we walk in with my friend Todd Nemet. He was like, this is unbelievable. Let's go watch the matches. I was like, watch the matches. I'm gonna go back out and figure out how I can sneak in again. Like, I don't want to watch the matches. I want to figure out how I can keep sneaking.

It was a challenge, right?

So that's just always been, like, what I'm into.

Embracing the challenge.

Embracing the challenge. Not going through the front door, dancing to a different drum, differentiating yourself, Being a different brownie. You know, you mentioned, like, handwritten letters. That's not in your life. That's old school, but it's not. It's really new school, because nobody gets handwritten letters anymore. So think about as a kid, how excited you are when you get a letter. You read all your mail. You don't read all your emails.

You know, that's so true.

Read all your DMs, but you read all your mail. You talked about. I forgot what you said about a car. You were saying something. I don't remember what you're saying, but, like, you know, if you drive an old car, there's a bazillion cars you're gonna see on the highway today. But if you see an old car, you're like, whoa. You know? Or a yellow car, you're like, whoa. So I don't do it just for the purpose of doing it. It's just. I recognize that different works, man. Different. And true to yourself works.

True to yourself is so critical. Yeah. So many people haven't learned to listen to themselves. Do you meditate? Do you journal? How do you tap into that inner voice?

I don't know, but I just remember telling people at Marquee, like, I would go to sales meetings at Marquee Jet Company we had, and I would listen to People pitch, and I'm like, you sound like me and Kenny, my partner. I'm like, you're a single mom. I co founded this company. Use that to your advantage. Talk about if you're quirky, be quirky. If you're shy, tell people. Or just, you know. But, like, don't try to, like, do my speech. I wouldn't do your speech. You know, you have to be your own version and then figure out within those parameters, people, like, it's relatable. I get. I just got a DM from somebody that's like, listen, I'm really introverted, and this is uncomfortable for me. And I related to that. I was like, wow, it's super honest, really vulnerable. And nobody else sent me something like that. Everyone's like, hey, I'm getting out of my comfort zone. I want to. You know, so you just have to be that. Find that common, you know, that ground.

That's. It reminds me of. My son was doing a speech, and the last minute, the school told him he had to change the speech, that his speech was too racy or whatever the word is they use. So with 24 hours before his performance, he had to take a very bland approach. And he was essentially reading it in a monotone because, you know, it's affecting him mentally. And you could see. See it on his body and everything. His quirkiness was gone. So I found out there was a speech teacher because, you know, they don't want. Kids don't want to listen to you in that moment. Right? Because he's no mom. You don't understand. I can't make this fun. And so I took him to a speech teacher, and she said exactly that. And it was so powerful for him to hear lean into that quirkiness. She'd let him do a speech talking about whatever he wanted, and he was tilting his head and doing this big smile, and he was animated. And when he read the one, he had to. He was reading it forced and monotone. And she was able to highlight and show them. When you start stepping into your quirkiness, the little funny things that are unique to you, everyone feels connected to you. It's so powerful. Oh, my gosh. I love thinking about how important being ourselves is for all of us. One of the questions that I like to ask everyone that's on my show is, when have you struggled in your life with your confidence the most?

I honestly struggle with it a lot still.

You do. Come on. That's hard. You have a very strong presence. That's hard to believe in Certain buckets. I do.

I mean, I've gotten comfortable getting. Having a lot of egg on my face. I've had a lot of egg on my face, a lot of failures and highly embarrassing stuff. I have. And when I was younger, I was.

Gonna say, that's not the stuff that comes up today, my friend.

Early on, I've had businesses that have failed, I've raised money. And that's really hard to tell people that it didn't work. You know, I've had projects, music projects that didn't work. You know, songs that flop, everything, but I think. So what was the question? Confidence.

When. When in your life, when you look back, has your confidence been the lowest or when have you struggled the most with it?

I mean, I just remember when I started out in the music business, I was in an airport coming in pa I landed in Pittsburgh for a show, and I was on the COVID of a magazine called Rap pages. And I was like, oh my God. I'm like, I'm on the COVID of a magazine. This is like, I gotta call my mother. Immediately grabbed it. I was super excited. And the headline arc was, are white rappers ruining hip hop?

Oh, no, it was me.

And I was like, I'm like, please tell me this is only in Pittsburgh. And it's like a national magazine. And I thought everywhere that I went, people would be like, this is the guy that's ruining hip hop.

We always think everyone noticed it. No one noticed it.

People notice. People notice. I mean, so that was. Took me to a low. I got dropped from my record company. I moved back to New York with no money. I was a kiddie pool. I mean, just everything I've had, I struggled with it. And I've always looked for small wins to get a little momentum to re. Perk. To perk up my confidence. I take inventory of things that I've done, you know, like, I'm about to run this big long ultra marathon and I'm struggling with, like, I'm not the same person I was when I was 38. Sure, I have luxuries now. I have an easier life now. I'm not as mentally. Like, I don't think where I was back then when I was really hungry, like, ridiculously hungry. And I did a 40 mile run yesterday, training. And I was like, I'm just not where I was this 12 years ago. And, you know, I don't want to embarrass myself, run this race, put myself out there and like, people like, what? You're supposed to be this, like, you did all this stuff and you only did like 20 miles, you know, and so, you know, there's that fear around how people are going to react and that's a confidence thing, you know, like that it starts to really attack your confidence. So I deal with it all the time and the way that I handle it is, fucker, you're not even in the race.

You gotta be in the ring if.

You want to give it a 7 billion people. There's 200 people signed up for this race and like, I don't care. It's like I've already gained so much in my discipline in the training, the friendships through my friend Mark and I that we've gone through in the training at night and the rain. It's already been a tremendous win for me, me. So I start to think, take inventory of those kind of things and then I'm like, you know, so that's one thing. And then I'm like, I'm gonna do the best I can do and lower expectations. I'm not, I'm not, and I'm not negotiating my, like my goal. I'm just, I've just been like, just be the, do the best you can do. Like you have four kids now, you have a job, you have a wife, you have parents that are getting older, you can't invest eight hours a day.

To train and that's okay.

And like just so be the best version of the 50 year old dad of four that you can be in this race, right? And if I do, great, great. But I'm not gonna, like, I'm not gonna quit, I'm not gonna like. But if it's embarrassing, it is what it is and like, I can live with that.

So what does the vision of your future look like now? And is there a specific goal, is there a specific amount of wealth you want to achieve? Is there a number that you chase out? What does that vision look like now?

I mean, it's definitely not money driven and it never has been.

Never.

I mean, I enjoy money. I like what money allows me to do, especially with my friends and family. Never. I mean, I have the same clothes, my same wardrobe. I have used my money to help me build an amazing portfolio of experiences. Yes, I have a bigger house, less worry as far as paying the bills, but I don't have Picassos. And that I've invested in, my time goes to experiences. If you looked at my last year, the trips I've taken, the mountains I've climbed, the paddle boards, the rivers I've crossed, that's what I like to do. But the next 20 to 30 years is just about putting more on my plate of the things I love to do with the people I love to do them with. And I have a course called build you'd life resume that I'm really passionate about because it's helping people. I give specific strategies towards business living, life hacks, etc. That's really important to me. And then legacy becomes important to me. Like I don't want to leave this planet. If I took all the energy I've invested since I'm 19 years old towards building businesses, making money, getting into rooms, convincing people to do deals and I channeled all that into something cause related. I mean I could, I think the impact would be valuable. And so that's something that's. I don't know what exactly that cause is yet or cause is, but that's something as I get older is really important to me.

Jesse, you are so interesting and your energy is powerful and it's so great to be around you. How can I know my listeners are going to want to get ahold of you? How can they find you?

Well, thank you. I'm on, my Website's just Jesse itzler.com that's where the BYL our course is. And I'm on Instagram at Jesse Itzler and all Twitter, Facebook, all under my name.

And I build you'd life resume is such an amazing course. I did it. It's really powerful. And you do live calls. Yeah, I mean that's a, that's a really unique advantage, this program. So please, if you haven't checked Jesse out yet, please check them out and check out the course. And thank you so much for being here with me.

Thank you for coming here. That's a different brownie.

That is.

We could have skyped but now we are connected through this experience.

I love it. Yeah, you gotta go the distance when you have the opportunity to jump on it because you never know what's gonna happen tomorrow.

Now I need a 45 second investment on a text from you and a handwritten letter.

Done and done. All right, thanks. We'll be right. I hope you loved meeting Jesse and I hope you're going to join me September 3rd at Hypergrowth Boston. Don't forget, use my code Monahan. If you want a free ticket, that's a 500 ticket. Holy cow. Jump on that. You know it's selling out. I don't even know how many codes I'm able to give out. So just grab it now while you can. If you're looking for other free things. Pluto TV is the leading free streaming television service. Watch over 100 TV channels and thousands of movies on demand completely for free. Pluto TV never even asked for a credit card. You don't need to sign up, you just watch for free. Pluto TV is easy and completely legal way to watch your favorite TV shows and hit movies for free. What are you waiting for? Never pay for TV again by downloading Pluto tv. You can download Pluto TV for free on all of your favorite devices today, including your phone, roku, Amazon Fire TV, Apple TV, Smart TV, PlayStation, and anywhere else you stream. My gosh, that's a lot of tv. So since I talked so much at the beginning of this show, I'm going to try to keep this tight for you so that you can get back to your life today. So thanks for hanging with me. One of the questions that I had sent to me this week came from a friend that said, heather, when you feel overwhelmed, what is it that you do? Do you start putting more pressure on yourself? What steps do you take? I'm having a really tough day. This is a friend of mine and here's what I responded. Number one, I put down my phone, I step away from the phone. I've learned that when I'm on my phone too much, checking social media, you know, reading media, whatever I'm doing, I start getting antsy. Another thing that I do is I step away from the phone is always helpful. I just go put it on the charger, whatever. Peace out. And then another thing that I do is meditate if I can. Now I work from home sometimes and if my son's home, there's zero chance that I am meditating because that's just not going to work out. So if that's not an option, another thing I love to do is to work out. I have a gym in my building so I can always run down to the gym, even just for 20 minutes and run on the treadmill or do the elliptical and listen to a podcast like mine. And you know, just getting stepping out of that negative space or stressed out space and moving my body always helps. Getting outside always helps. I live in beautiful Miami and while it's pretty hot right now in the summer, it still is amazing and I feel really grateful when I'm outside. Stepping into gratitude is always an answer to calm myself down. Looking at how far I've come is another thing that I like to do. And I keep actually a journal on this of the things that I've accomplished. I also keep on my phone. I recommend everyone do this. You know, if you keep by year the things that you did, it blows you away when you see all of the change and accomplishments and yeah. Challenges and solutions and how you overcame things. So I go to these different albums on my phone. I also keep positive feedback that I get from people that's meaningful and special to me. It was so cool. I got a note actually yesterday from my old boss and mentor. Jeff sent me a screenshot. His father listened to this show creating confidence and sent him a note and said, hey, I don't know how I found creating Confidence with Heather, but I remember she used to work for you. And I just want to say her show is great and she's a really smart, powerful woman. And it was just. It meant the world to me because this is someone who I looked up to. This is his father who he adores and looks up to. And it was just. It was so meaningful and so sweet that he sent me that feedback. So that went right into my fam love. I call it my Fam love album. And whenever I'm feeling down, overwhelmed, I read through those notes and it really picks me up. So the next time someone sends you a nice note or you have a grateful thought, jot it down. Put it in a file or folder like that so you can access it quickly and it definitely works for a good pick me up. So. So again, I hope you join me. September 3rd, Hypergrowth, Boston. If you want a free ticket, type in the code monahanallcaps. I don't know how many free tickets there are going to be, so please jump on it right now. If you can join me, I would love to see you there. And until next week, I can't wait to see you creating your confidence. Love to hear your questions, love to hear feedback. If you haven't, please subscribe, rate and review the show. It helps so much. And please share with your friends until next time. Keep creating your confidence.