Robert Leonard 1:50
Through all of your success as an entrepreneur, what have been some of the biggest lessons you’ve learned firsthand that could help a millennial listening to this show who wants to become an entrepreneur?

Jesse Itzler 2:00
First of all, things take time. I think there’s a big misconception that everything happens overnight. And I remember when we started out with ZICO and I went to meet with the President of Coca Cola, and he’s like, “It’s going to take you guys eight years to build the brand in this country.” And he’s right. There are exceptions to the rule but most things take time. And I thought, like, “Oh, you start a business, you do everything, right. And it just blows up.” It doesn’t work that way. And I think there’s a lot of confusion around passion.

I think people confuse passion for what they’re selling or doing, but the passion has to be around the journey, you know, the good, the bad, the struggles, the time. All of that is what you’re signing up for. And you have to be down with all of it, the good and the bad, and the late nights and all that stuff. And just to appreciate that that’s what you signed up for and have a great attitude around that. I think that’s really important. I think you got to get a little lucky. I think you got to create your own luck as well. Put yourself in a position where luck can find you and you got to have a great idea and be able to tell the story.

Robert Leonard 2:58
Not only have you been successful yourself as an entrepreneur, but you’ve also been able to see behind the scenes of your wife, Sara, growing her company Spanx over a billion dollars. What have you learned from watching her grow her business?

Jesse Itzler 3:10
I should have married her earlier. She is an amazing story. And she’s someone that has done everything that I just said, you know, tremendous passion. She’s obsessed with her product. She’s obsessed with providing value to our customer. She’s obsessed with the story around that, you know, it’s authentic, helping women. And she’s very good at what she does. So I mean, like, Sara’s success didn’t happen overnight. Her journey started when she was a little girl, working on herself, doing all the inner work that she talks about that she did.

And you know, when it was her time, she was very ready for it. And a lot of people might have their moment and they’re not ready for it. You know, I’m pitch ready, 24/7, I’m ready to pitch. I feel like that’s an important thing is you have to be ready for the moment to take advantage of.

Robert Leonard 3:58
You mentioned that you live with the SEAL and then you later live with monks, and then you eventually wrote books about them both. Why did you want to do that? And what were some of the most surprising things that you learned from those experiences?

Jesse Itzler 4:09
Well, I’m a big believer in building your life resume and not your traditional resume. I mean, a traditional resume is important, obviously. But the reality is, most Americans work 40-hour work weeks, and that still leaves about roughly 75% of the week to do other stuff. And we focus so much on that 25% that’s work or 30%, whatever the number is, with sleep and this and that, and not enough on all that other time that we have. And I’ve always felt like, I’ve just invested in experiences. It’s always been something that made me feel alive. It’s always been something that’s helped me at work, it’s made me maybe a better father, a better businessman, a better boss, you know?

It’s not a matter of feeling satisfied. It’s just a matter of like, what’s next. Like if you didn’t bring up, mark my past. I don’t even have a Marquis Jet hat anymore. It’s like, it’s what’s next. You know, it’s from today until my ride is over, my journey is over. It matters to me. And what I’m focused on and how can I build that and squeeze everything out of that. And that’s sort of how I approach everything. If I went through my day today, from the minute I woke up at 5:45 to right now, eight o’clock at night, when we’re talking, there wasn’t a minute really to dilly-dally, like it’s packed.

I just took my kids for football, took them for a walk, took them to the swing, putting them down for bed. It’s like I work the full day. I ran twice, I swam, I had meetings, everything… My parents are here, I spent an hour with my dad in the pool. Like, every minute. And it’s not always like that. I go to the beach too. I slow down. But the majority of my time is like 50 days and what, I feel like I’m 470 years old in how I’m living my life.

Robert Leonard 5:45
And one of those experiences that you created that I think is incredible, and I’d love to talk to you about it more is Everesting and that’s through your Events 29029. Can you talk to us about that experience and why you do that?

Jesse Itzler 5:56
That’s a business I started two years ago with my partner Marc Hodulich. We rent them out, we take out the whole mountain, you climb up to the top, you take the gondola down and you repeat, until you climb the equivalent of Mount Everest, 29029 feet. We bring in speakers and bands, music and food. and etcetera, and create our own little festival around this event.

I feel like three things come off it. For one, for those that do this with a friend or a group or even come alone and meet new people, those bonds are unbreakable, that are forged through the adversity of the challenge. When you leave that you feel like you can do anything in the world, because you push yourself further. I mean, the average finish time is 27 hours. That’s basically seven marathons as far as time. So I feel like people leave there and they just feel like they can conquer the world. And that’s the sign of a really good event.

Robert Leonard 6:49
I personally have enjoyed many, many things that you’ve written about or talked about. I’m a big fan of yours. But one of the favorite things that you talk a lot about is this idea of the number of times you have something left. And that was something that was in the back of my mind as you were talking about how busy your day was, and whether it be going on a trip or like you’ve talked about, going to visit your parents, you often break down the number of times you truly have left of each activity. Can you talk to us more about this idea and why it’s so important to you?

Jesse Itzler 7:16
My relationship with time is when we think of relationships, we think of them in terms of people, as your relationship with your dad, or your mom, or your kids. And that’s super important. I also think your relationship with time is very important. I think for a lot of people, we think the notion is we have a ton of it. And the reality is we don’t even know if we have tonight, you know, but no one thinks like that. If they did, they’d have their graveyard picked out. They’d have their pass codes handed out to their loved ones, but no one thinks it’s going to happen anytime soon.

So my relationship with time is I’m very aware of my mortality. I’m very aware of how long the average American lives, which is 78. I’m very aware of that. So it’s created a lot of urgency in my life, but more importantly, it forced me to focus on moments, not minutes, or hours or days. So I mark my moments. I’m always saying to my friends, remember this right now, we might not ever jump in this lake again. We might not ever run this race again. We might not ever be in this room brainstorming this business idea.

Mark this moment in your head as a moment that we remember. I say it all the time. I’m an encyclopedia of moments. That’s how I look at it. You know, I look at my parents, you know, they are about to be 90. As my dad or my mom live five more years. I hope they live forever. And I see him twice a year, I don’t know, five years, I’ve 10 visits. So that’s sort of how I put it in a box. Now millennials, young cats out there are invincible. This might sound like a little bit crazy. But as you get older, you’ll start to realize people tell you it goes fast all the time. You don’t need me to say that life goes fast. But the younger that you realize how important those experiences are, and you take advantage of them at a young age, then the more rich your life will be because you’ll have more experiences and memories and at the end of the day, what more do you want than that?

Robert Leonard 8:59
You know, it does sound a little crazy to somebody like a millennial. But I remember the first time that I heard you say this and talk about this. And ever since then it’s always been in the back of my mind, I think I can do better at it. But it’s something that I always try and live my life by.

Jesse Itzler 9:15
Let me ask you a question. In the last five years, from 19 to 24, what are the five biggest things that have happened in your life?

Robert Leonard 9:22
I’d have to say graduating college and buying my first real estate investment property. Of course, there’s more than just those two things that have happened over the last five years. But it would take some time for me to think back as to what they are.

Jesse Itzler 9:35
See what I’m saying? You’re not even going through it, man. You live in like, boom, you went from 19 to 24, but two moments. You live 1500 days, and you just told me two things at a 1500 days. So that’s my point. You’re not alone. Most people can’t remember what they did days ago. So what I’m saying is, these moments are so important because otherwise you’re just going through it and it’s like you’re going from A to B like nothing happened. And then there’s 1500 days, ups, downs, wins, losses, trips, family, emotions.

And once you realize, 19 to 24 went like that, you know, you should be able to rattle off 30 things instantly. And they don’t have to be like I climbed Mount Everest. They could just be like, :Oh my god, I was on a boat ride and I got emotional. I did this, I did that, whatever.” But like, for millennials, just look back on your own life, like what did I do this year? I had a whole year, what did I do? What were the three or four things or five things that defined this year? And if you can’t pick them out, you got to relook at how you are living your years.

Robert Leonard 10:38
I’m actually leaving for Disneyland on Monday. So that’s going to be something. I really need to plug into that experience and take your advice there and really make sure I’m fully involved and not on my phone. Not on my computer. I’m really involved in that experience.

Jesse Itzler 10:50
Don’t give up your 20s, man, you’re 24 years old. Don’t all of a sudden wake up and be 30, and be like what happened to my 20s? Don’t be 40 and be like what happened in my 20s and 30s? Certainly, don’t be 50 and be like what happened in the last three decades? Because at 50, everything starts to break down.

Robert Leonard 11:06
Is this what you mean by building a life resume?

Jesse Itzler 11:09
Yes. I don’t know what could be more important. It’s like you’re here to live. You’re living to live. Your job is to live life. And you could make an argument that it’s easier for me with money, but I was 21 also, and honestly, my life hasn’t changed much other than I got a bigger swimming pool. Same friends, same activities, just ran an ultra marathon, running another one. In four weeks, my calendar is full, my day alone was stacked. My day alone was a lifetime and a day to day. I went through every emotion today that I would go through in a year, every day.

Robert Leonard 11:42
And so what keeps you motivated to continue to do those things?

Jesse Itzler 11:45
I love it. I love the feeling of being alive. I love the feeling of challenge. I love the feeling of newness and pushing myself. I love relationships, gratitude. I mean, like I was listening to a Wayne Dyer episode the other day and one of his guests are like, “Every day, you should live in all.” And I was like, I totally get that. You know, like there’s so much to be amazed by and I feel like I got bit by that bug. I feel like the amazement bug bit me right in the arm and said, “You better appreciate this because I feel super lucky.”

Robert Leonard 12:16
Yeah, it’s just innate in you. So it’s really interesting that you say that because I was listening to Gary Vee the other day, and I’m not sure if you’ve heard him say this. But he says something similar about how it’s just when you think about it, you won the ultimate lottery becoming a human on Earth. If you don’t value that, then you’re just absolutely passing up on the most amazing thing ever.

Jesse Itzler 12:34
Yeah, I mean, that is definitely true. I definitely feel that way. Part two of that is how do you extend it out? Understanding it is one thing. We definitely win the lottery. Now, how do you live your life?

Robert Leonard 12:45
And it’s by making those experiences?

Jesse Itzler 12:47
Well, I just think that you know, everybody has the same 24 hours and I’m sure Gary’s looks different than mine and yours, but you know, I don’t think it’s a one size fits all. But for me, I always, always work in time for myself, trips for myself. There was always that balance. It was never work. And then all of a sudden I was 30. There was always a race, a marathon, a fishing trip, my buddies, there was always all of that.

Robert Leonard 13:13
Do you have any advice as to how you can keep those balanced?

Jesse Itzler 13:17
It starts with wanting it and planning it. Like my day starts the night before I map out my day. It’s so tight. I’m not winging it. I’m not going through life like winging it. It’s scheduled. I know what I want to do. It makes it a lot easier. If I just woke up and said, like, “Well, what am I going to do today?” It’s mapped out, I know, tomorrow, boom, get my kids ready, taken to school, 10-mile run, work. I have it all laid out all the way through bedtime. So well done. It’s got… just do it. And it’s around what I want to do. I mean, I’ve worked, I can’t move certain things. I have meetings, but the other stuff, they’re like electives in school. You have to do physics, you have to do calculus, you have to take those courses, you know, but then you have the electives that you love to do. So every day my electives are scheduled in, you know? Of course, I have responsibilities. Of course, I have work, a lot of it. But then I layer in the stuff that I want to do.

Robert Leonard 14:07
Do you schedule in your family time too?

Jesse Itzler 14:09
Absolutely, 100%, everything, I schedule it in. I basically end my day at five o’clock. So the rest from five o’clock on is with my family, until eight o’clock in the morning, it’s with my family. So 6-8, two hours, and then really 4:30, my day ends, I shut it down. And then until 8:30, five or six hours. Six hours is 25% of the day, and it shows. The relationships show. But look, now I still have 18 hours in the day. I take three for myself, I sleep six, and the rest of it is working other stuff. And that’s the general scheme of my day.

Robert Leonard 14:51
I absolutely love that. And I think the earlier you can learn it, the better off you’re going to be because then you have it for the rest of your life. If you’re a millennial, you still have your whole life ahead of you and you can learn it now. You don’t want to be 50 and looking back on it, just like you said.

Jesse Itzler 15:05
Here’s the most important thing in that formula. It’s the three hours for myself. Because if I don’t take time to do the things I want to do, I’m going to resent my wife, or my boss, or my work. But if I can do the things I want to do, then I’m going to be super present. I’m going to be where my feet are with my wife. When I’m at work, when I’m with my kids, I’m with my kids, because I’ve already done the things I want to do. If they took away my running, if they took away my reading, or my alone time, I’d be mad, it won’t work for me. Once I checked that box, the me box, I can give it all work. I’m not anxious to get home to go for a run or getting a song or just chill out. I’ve already scheduled that. It takes all the pressure off. I still know I’m going to get my timing. And that’s a really fundamental principle on how I live my life, since I’m 21, unwavering. I take two or three hours a day for myself.

Robert Leonard 15:55
And are those just hobbies, like hobby hours?

Jesse Itzler 15:58
It’s cumulative. So it could be 15 minutes of doing nothing, it could be an hour run. So when I’m in my time, I’m not guilty that I’m not with my kids or my wife, but when I’m with them, I’m super present.

Robert Leonard 16:09
I love that. That’s something I need to work on myself. I think I mix the two too much. So I definitely need to work on that myself.

Jesse Itzler 16:16
I understand that everybody has a different system. But what I’m saying is, being aware of those hours, and making sure that you carve out a little bit of time every day to do the things that you like to do. I don’t know anyone super successful that doesn’t do that.

Robert Leonard 16:30
Yeah, I was just going to say that a lot of the people that I’ve talked to or listen to, they all have similar ideas. They schedule their days, they make sure they make time for themselves. And it seems that this is a repeating theme for people that have been ultra successful. So…

Jesse Itzler 16:43
They did a poll of people that had a net worth of over $25 million liquid, so like really successful people. And they asked them what was the number one thing that they regretted on the journey to make all this money? And the answer was the sacrifice to their family and to themselves.

Robert Leonard 16:59
So if you were to summarize everything you’ve learned over the years, and being an entrepreneur and owner of an NBA team, a father, a fitness enthusiast, and even a rapper into just one piece of advice, what is the number one piece of advice you’d give a millennial listening to the show today?

Jesse Itzler 17:17
Don’t waste it. There’s no do overs. You don’t want to look back and be like, I was the 80% version of myself when I was 24. If you want to take 24, and you know, drink, smoke, party, the bus doesn’t care, man, it keeps going. You want to go out, mess around, whatever. And then one day the bus stops. And like, if you’ve already lived this much your life and you only have this much left, this is your whole window. My advice is take advantage of the opportunity. Like you should be wired for the opportunity, the value of the opportunity.

Even now in my life, when I look back on these businesses and some of the successes and some of the failures, it’s still the same philosophy. I’m 51. It’s like how do I maximize the here to here. How do I maximize from here to here? Like I want to be a millionaire by the time I’m 28. My window went from 22 the day I graduated to 28. How do I become a millionaire before I’m 28? And that was a shorter window. Now my window is not about the money. It’s about maximizing that with my kids, with my family, with the experiences, etc.

Robert Leonard 18:21
Jesse, thanks so much for coming on the show today and providing a ton of value for the audience. I really appreciate it. For those who want to learn more about you and all the different things you have going on, where should they go to find you?

Jesse Itzler 18:31
https://jesseitzler.com/ and Instagram, my name is @jesseitzler for Twitter, Facebook, Instagram.

Robert Leonard 18:39
I’ll be sure to put links to all of that in the show notes. Jesse, thank you so much for your time.

Jesse Itzler 18:43
Thank you so much for having me.

Robert Leonard 18:45
This has been another episode of Millennial Investing. If you enjoyed this episode, you can really help the show grow by taking just 30 seconds to leave a five star rating and review on Apple Podcast. This really helps more people discover the show and allows me to continue to bring on the absolute best guests for you all. I greatly appreciate the support and I look forward to seeing you again next week.

Outro 19:07
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