Preston Pysh  7:36  

Jesse, you mentioned the idea of time kind of standing still. I noticed that this was a really common theme throughout the book.

Talk to us about this idea because I found this really profound and kind of really important to the underlying point that you’re making in the book.

Jesse Itzler  7:52  

When we think of relationships, we think of relationships in terms of people, “Oh, my relationship with my mom, or dad, or my wife, or my kids.” We think of relationships really in that way, as it relates to our human relationships. 

However, very often, we never really think of our relationship with time or our relationship with money. Those are two big things in everybody’s lives. 

I am very aware of my relationship with time, especially as I turned 50. It’s not a midlife crisis or anything like that. I’m just aware that the average American lives to be 78 years old. That’s a fact. I’m turning 50, so I hope I’m not average. But if I am, I had 28 summers left.  

I just climbed Mount Washington. I told you guys that story. There were no 70 year old guys on the mountain. I just ran this crazy race. There were no 70 year old guys in the race. 

When I think about it that way, well, then, yes from 70 to 80, you cannot probably do what you can do in your 40s and 50s. And so, if you look at it that way, well, then I really only have 15 or 20 really relevant or prime years or quality years in the sense of doing the things I want to do. I sleep a third of them and a lot of my weekends are taken up with responsibilities. 

When you think backwards, you realize that, “Wow, my window is shrinking fast.”

Even in your 30s and 40s, that’s why you wake up. If I were to say you guys, *inaudible*, I don’t know… That was six days ago. You’re going so fast. You can’t remember how long. 

One thing that I realized for myself is like my parents are 88. They’re older and they live in Florida. Most people don’t live that close to their parents. You live close to your parents, Preston?

Preston Pysh  9:48  

No. They’re in Florida. 

Jesse Itzler  9:50  

How old are they? 

Preston Pysh  9:51  

Around 60?

Jesse Itzler  9:52  

How many times a year do you see them?

Preston Pysh  9:55  

Once or twice a year.

Jesse Itzler  9:56  

Okay, so if you see him once a year, and they’re 60 then they live to be 78, you don’t have 18 years with them, I mean that you do. But really, if you look at it in moments that in time, you only have 18 visits with them.

When you look at time that way, and you’re like, “Wow, I might only see my parents 18 more times.” That might not be acceptable and you might make changes. You understand what I’m saying?

My parents are 88. If I see them twice a year, and they live to be 92, I only see them eight more times. I’ll be on a plane to see my parents, when you start to think of it that way. 

My point is, I’m very aware of time. Very aware of it. There’s not a day, not one single day, when my head is on the pillow at night, when I don’t look back and take a little inventory of did I waste the day? Did I maximize the day? Did I do my best today? Did I spend my time with the people I want to spend it with doing the things I want to do? That’s sort of my thought process.

You hit a hot button. Time is a hot button for me because everyone’s like, “Oh my god, I went so fast.  I can’t believe I’m turning 40 this is. My kids are all grown up.”

We don’t stop to take inventory of amazing moments. You and I shared an amazing moment. We climbed a mountain, but I was very aware at that moment that this was happening, that this was going to be something. We have a relationship now that’s different than it was. 

A part of that is because we were both aware that something amazing was happening. I take inventory when that stuff is happening. When there’s a great moment I take a minute. There’s an appreciation and then it registers. Then I do know what I did on April 18, because it’s not just like happening so fast that I’m flipping the calendar. 

When I went up to the monastery, time stopped, because there were no other options. When you get out of your routine can go slow. When you’re in your routine, time goes fast. I was so out of my routine and had so much time to think that you start to realize what it is that’s important to you. More importantly, how much time you spend on things that aren’t that important to you.

Stig Brodersen  12:28  

Jesse, I really like your point about moments and building these powerful moments. Now, I didn’t share one of those moments with you guys climbing the mountain. One of the main reasons is that I don’t have the same negotiation skills as you do with your wife. 

However, I do want to share one moment with you that I never shared with anyone else. That’s about our next question. 

The moment is the first time I ever say “naked pool discussion” in my entire life. That’s the moment I shared with you yesterday. 

People who might be sitting out there might be wondering what I am rambling about. Jesse, tell this amazing story about how a businessman has had a profound impact on you when you were in your 20s. It revolves around a very naked pool discussion. I just said for the second time in my life there just because I could. Please tell that story, Jesse. 

Jesse Itzler  13:27  

I was in the music business. I didn’t get picked up for a second album. I moved to New York City from California with very little money at the time. I was living on my friend’s couch. My time had run out. He told me as of Monday, his roommate really wanted the apartment back. I had to find a place to live. 

That weekend, I was at a bachelor party in New Jersey. I was at a bar with my friends and ordering a drink. Then a girl came over and we just started talking and she asked me where I live. I told her actually, as of Monday, I had nowhere to live. 

She took out an app, she wrote her address and said, “Hey, if it’s truly an emergency, you can come stay with me.” I just met her. I never met her in my life. I laughed and I said, “Is that a real offer?” She said it is. On Monday morning, I woke up and I said, “This is an emergency. I don’t have anywhere to live.” 

I took out her address and I literally showed up with my one bag of stuff.  I lived with her for six months. 

During that time, I continued on in the music business from her couch, but I was it a really critical junction. I just wrote a song for the Nets. It caught on a theme song. Other teams were calling for me to write demos, with the hope that if they liked my demo, they would buy this song for themselves.

However, I had no money to go in the studio and make all these demos. I couldn’t grow my business. I then went to a music manager and he said to me, “Look, I’ll give you $10,000. I’ll lend it to you in cash, but I want 10% of you like forever.” I was stuck and with no money at 21 years old, this guy had some connections, I was like, “Absolutely, this seems like a great deal.”

Before I did that, I went and talked to my roommate. This girl’s dad, who was a big business man and had some entertainment connections. He’s a really, really successful guy. I go to his apartment in New York City and I walk into the apartment for the morning meeting. He’s got all these amazing, like… I’m not into art, but I could tell that his collection was “The Art.” 

He was *inaudible* books on the walls and all this amazing furniture. I went into his room where he was, he had a little bedroom. He was in his penthouse apartment. He comes out of the pool for a meeting naked. He had a swimming pool, a lap pool in his apartment. He came out naked, which was… I didn’t really know him that well, with no problem starting to talk to me. 

He puts on these little skimpy shorts, starts running on a treadmill and talking to me. I tell him my situation. I have no money. I have maybe $100 at the time or something. I told him this guy offered me the money, what would he do? He got off the treadmill. 

He said, “You know what, Jesse, I would trade everything, except my kids, everything that I have, the art, the pool, the private plane, for the one thing that you have?”

I said, “Me? I’m broke. What are you talking about? Well, what’s that?”

He looked me dead in the eye and he said “youth,” the process, to be able to go through the entire process of figuring it out, not knowing, being able to take risks, failing and winning, and making new friends. The whole process of what you’re about to go through. I will give it all back. 

That really stuck with me. Then he said to me, he gave me the litmus test. He said, “Would you bet everything, the farm, everything you have your whole life, your name, your reputation, everything on the fact that you will make this project work? Can you make this thing work?” 

I said to him, “I think I can make it work. Yeah.” 

He said, “You can’t think. Will you make this project work no matter what? Look into the future, look into your heart. Look past, again, your ego.”

I really look deep into myself and decided I will make this work without question. Then he said, “Forget the 10 grand. Go do it, figure it out, start the process.”

That was the start of my entrepreneurial journey. I said, “Keep your 10 grand, it might take me a little longer, but I’m going to enjoy the process.” I have ever since. 

I was reading the audio part of my book. The other night I had a deadline. I was going to be in the recording booth for nine straight hours. This is after seven hours, the past two days in this little tiny booth. All of my friends were going to go watch the NBA playoffs. Everybody was going out. I couldn’t. I had a deadline. 

I just said to myself, “This is what I signed up for. This is still part of the process. This is what being an entrepreneur, trying to get this project done and completed to my satisfaction is all about. This is what I signed up for. There’ll be other basketball games.”

Stig Brodersen  18:42  

Thank you so much for sharing that story. The very first time that we had you on, Jesse, you talked about loving the journey. You talked about being a rapper. Being a rapper was not about receiving awards. That might have to sound, but it was like all the hustling. You got to love the journey. 

It’s really been an inspiration for Preston and me, speaking to students and speaking to new professionals going to the finance industry. They’re asking, “What can we do to really advance and be successful in this?”

I always refer them to your response: Do you love the journey? 

You probably won’t be surprised when I tell you that a significant part of the people who come and ask us, they do not like the journey of being in the financial sector. They might like finance, but they don’t like the long hours. They don’t like the sacrifice. It’s all of it. You have to immerse yourself in the entire experience.

Jesse Itzler  19:41  

I agree. I think everybody has a different definition of success. 

One definition is sort of what I said earlier: you wake up in the day and say I’m going to give it my all today. At the end of the day look back and say, “I did.” Is success an effort or is it a success result? Or is it both? Or is it happiness? There’s so many ways to grade it. 

One thing, I’ve been very fortunate to help my kids get this message and I hope my friends and those around me get this message is there’s only one script. You’re born, we’re all dying. Some might die faster, some might live longer, but I am pretty confident that in 110 years from now, nobody on the planet right now, our age, will be around. 

A lot of the worry and things that we do day to day, it won’t be relevant to the next generation. I love my grandma, but I don’t think about her struggles. I think about my struggles. Her journey has ended. 

I think that if you go through that one script, without rewrites, to make it the script that you want, you could look back with a lot of regret. Now I understand everyone has to make a living. I understand you have to sometimes take jobs that you don’t love, but to stay in a situation like that long term, without trying something differently at night, or working on something at the side, or trying to make a change or downsizing and taking something that you do like but living differently, which might make you happier, that’s a really tough place to be in. 

I have a ton of friends in finance who make a lot of money and are miserable. We all know money is not the end all means to happiness, but I know a lot of people that are miserable in what they do, and they just stay in it. Then all of a sudden, they’re 60. They think they’re having fun, or they had fun, but they don’t even know what fun is until they experience fun. 

When you have an appreciation for the process, even the bad things that happen, the bad days, as an entrepreneur, I have plenty of bad days, and plenty of things come that I can’t control and I have to deal with. 

The toilet might overflow one day, I have to deal with it. My wife looks at me and says, “Fix it.” I didn’t plan on that, but my point is that I agree with you, Stig. I agree with you. 

Once you have that mindset shift to this *inaudible* to be grateful and to be in the position even go through the process. 

Look, you guys started a podcast. I’m sure it wasn’t easy. It still isn’t easy. Finding guests growing your audience. You want to put content out there that people enjoy. That’s probably your mission statement, right? That’s what you guys are doing. It never really gets easier, but you still have the love for it. That’s the backbone and the foundation of anything that you do.

Preston Pysh  22:36  

Jesse, in the middle of the book, you have a quote that you published there, what Brother Christopher had said to you. I don’t know if you can recall which quote I’m referring to, but you’re talking about this experience. He said something really profound to you. Can you tell us what that was?

Jesse Itzler  22:51  

Yes, I do. I think you’re referring to when he said to me, “When you talk, you’re only repeating what you already know, but if you listen, you may learn something new.”

He said that to me early on. It made me realize that I’m not a great listener. Very often just by observing and listening at the monastery, for example, I learned so much.

u\Isually I’m a talker, I’m a seller, I want to talk and it’s about me. I realized that there was a lot of work to do and I could really grow, which is why I was there and invested these days for personal development to get better. I really needed to become a better listener. 

When I became aware of that, and started to just kind of slow down, even when I got back, and even now, I even noticed in the opening of this podcast, I was so eager to jump in. I was like Jesse, listened to Stig and Preston and enjoyed the intro. There’s just a tremendous amount of growth that comes from listening. I realized that I struggled with that for 40 years of life. I don’t want to listen.

Preston Pysh  24:06  

I can totally empathize with that. What was a game changer for me personally was doing the show when we had to go back initially, and we had to listen to ourselves. 

Stig is laughing because he knows exactly what I’m talking about. 

The first thing I noticed when I had to listen to myself was I interrupt people so much, and it was really annoying. Then after I do the show 200 times or whatever, you really start to understand how important it is to just shut up and just listen to the other person. 

It was a very hard transition for me. When I read that quote, I was just like, “Wow, that is really profound and is just such an awesome quote.”

Jesse Itzler  24:47  

Yeah, it’s still something I’m working on. It is hard but when you become aware of it. Now I find that I can learn and this is kind of what his message was. 

By listening you can learn from anyone or anything, if you allow yourself. I never allowed myself, but now I really have slowed down, sort of, but I have an understanding and awareness to listen and become more aware of my surroundings, of people, and not just experts. I think that was part of his message too: you don’t always necessarily seek out experts. There are lessons all the time everywhere, every day, if you allow yourself to listen and I did.

Stig Brodersen  25:37  

It’s very interesting what you talked about earlier too about what is success and what’s right for you, Jesse might not be the same thing that makes Preston *inaudible*. One thing that is so popular these days is really talking about happiness, which in many ways is probably kind of concerning, because that probably means that thing is missing in our lives.

However, in your book, you told the monks two stories about events that took place in your own life. Would you mind sharing those stories with your audience?

Jesse Itzler  26:09  

Sure. I was explaining to the monks at some time that we had together that my first job…This is crazy, but my first job was as a breakdancer. I grew up in New York in the 80s when really hip hop and breakdancing really emerged. 

Preston Pysh  26:28  

Jesse, how old are you at this point? 

Jesse Itzler  26:30  

I was 14 or 15, sophomore in high school. It really started to get momentum. I’m not going to talk about pop radio momentum. I’m just talking about momentum on a street level. 

I decided that I wanted to go to Washington DC to break down because I figured there’s no way the kids in DC could be as good as the kids in New York. We invented this.

I convinced my sister who just got her driver’s license to drive my friend Myron, who’s part of my crew, and myself down to Washington, DC to breakdance and to make some money. Then we’ll come home.I

The whole time down there, I’m struggling with being nervous, but no one shows up. We’re all the way so far from home. We show up in Georgetown and we go to this little parking lot in the bank. We have our boombox and a cassette. We set up the boombox, we push play, and a little crowd eventually starts to show up. Then a bigger crowd shows up and I do my thing. I pass it to Byron and he does his thing. He sends it back to me. We go through our whole routine and then we do it again. We only had like a 30 second routine. We did it like 40 times. 

I took off my hat and I started passing it around collecting money. At the end of the day, we collected around $260, something like that. We gave my sister the gas money for the trip down. Then we took out money for food and money to get home. 

Then we had about… I think it was $82. We had $41 each. He starts counting all the *inaudible*, all the way to 41. Then he puts it in his pocket and he sprints over to me. He gives me a bear hug. He looks at me and he goes, “Jess, we’re rich. We have $41 each.”

I told the monks that story. I said, “Fast forward about 20 years later and I got a call from my partner. We were selling our company, Marquis Jet, to NetJets.” I was explaining to them that I wasn’t really much happier at that moment than I was as this 14 or 15 year old kid that made $41. 

The obvious answer is that money’s not going to bring you happiness, but I realized that if I worked hard and something that I liked and offered something that was positive to the world…

My wife always says you find your purpose at the intersection of what it is you love to do, what you’re good at, and something that you’re offering to the world that’s positive. 

In that little breakdancing moment, it was something that I love to do. I was decent at it. People were reacting positively and I got rewarded for it. It felt amazing.

At the Marquis Jet experience, yes it changed my life. But the passion… I never really loved selling time on airplanes. I just didn’t. I didn’t feel like I was put on earth to sell time on private jets to people who can afford it. I just never loved it. Even though the end result was way different… It was in need of this windfall, all the way in the other direction. 

Stig Brodersen  29:51  

Quick thing, it really reminds me of the story that Tony Hsieh talks about in his book “Delivering Happiness” when he sold his first company to Microsoft. He was like, “Yeah, I was eating this burger with my roommate and business partner. We sold it… Let’s do something fun now.” 

It was kind of like your story because it’s not about the money. I guess it was just not a thrill anymore.

Jesse Itzler  30:21  

I recently took my son who’s eight to climb Mount Washington, which is freezing. We camped outside in the winter and in the snow, and it was minus five degrees. We had crazy sleeping bags to keep us warm. 

I went with my friend Kevin who is a police officer in Suffolk County, New York, and his daughter. The four of us went. When we got to the top of the mountain, we were camping out. I was so cold, I can’t even explain it. 

We’re all in our sleeping bags and fumbled up. Kevin is a blue collar guy. He’s a police officer. He’s been doing this forever. He doesn’t come across a guy that’s focused on money or accumulating money, but he’s one of the happiest guys I’ve ever met. 

I said to Kevin, “How many of these trips do you take a year?” He goes, “Well, every year I take a trip with my high school friends. We’ve been doing it since we were 21 years old.” 

I’m like, gosh, I need to do that. I don’t do that. I want to do that. He added, “I take probably six other trips a year. One time, one weekend, every other month, I take a trip. I go to LA to run the marathon. Maybe I go hiking with my family, maybe I’ll drive to the canyons, whatever. But I put it on my calendar every other month. I call it the Kevin Rule.”

I thought then, “If I can take one weekend, every eight weekends, put something on my calendar that makes me happy or create a moment, like we were talking about, then the script is broken. I got to rewrite.”

Kevin can work seven hard weeks or whatever, but he knows at that eighth weekend, he’s going to do something he loves with the people he loves to do it with. It’s so simple. Yet, we barely ever do it. 

We live in a world of “on vacation time I take a week off” and that’s it. We live in a world of but all these opportunities and weekends.

Most of the things that we do, but he did does, and I didn’t. It doesn’t cost him anything at Mount Washington, because nothing. The parking is free. Yes, you have to buy a sleeping bag. You have to get some boots, but it’s not like you flying first class to Europe and staying at the Four Seasons. It was more fun. 

My point is he’s got this five, I call it “The Kevin Rule.” this five or six weekends a year and it helps. Those things help.

Preston Pysh  32:43  

You’re talking about simplicity here. This was another major theme that I saw in the book was when you’re living with the monks, they were just really simple in everything in every way that they do anything. They keep a very systematic schedule. It’s almost like a programmed kind of schedule. 

After you went through that, why? What’s the advantage to that? Is there an advantage to that? What’s your thoughts on it?

Jesse Itzler  33:09  

Well, I think I will answer this in two ways. For starters, I live in a world of multitasking. I’m constantly doing multiple things. Spend five minutes here, jump to the new list, cross that off, go back to work. I’m always multitasking. 

The monks monotask. They are so focused on quality over quantity. They don’t really have time restraints around. When they’re going to finish, they’re finished when it’s done to perfection. 

Their job was to clean the church. It’s like I will clean the church for 15 minutes. I’m going to clean the church and I’m only going to focus on the church. I’m going to be done when the job is done, but it wasn’t so much centered around time as it was around quality and completion. 

For example, Brother Stavros will say, “This morning, I’m going to clean the church.” It wasn’t like I’m going to clean the church, then here are 15 other things on my to do list. When I’m done with that, I’m going to go to the next item, but I’m done with that. That’s done. Off my list and it’s done to perfection. 

Every single task they did, they did with every ounce of their soul. I’ve never seen anything like it. It could be organizing the books in the library. I can stack them up. They would stack them up and push them in and make sure they were in  order. Then they would come back and look at it and they would clean the books. They would write the number on the books. It was amazing.

Preston Pysh  34:40  

What is it the culture that made them do it that way, like how can we extract that behavior into our own lives? What is it that they have that made them that way? Is it just the culture?

Jesse Itzler  34:50  

I think it’s a little bit of the culture, the culture being that everything is theirs. They have pledged all their possessions to the monastery. They own nothing. They own a driver’s license. When they clean up the books, those are their books and their bookshelf. They treat it like it’s theirs.

There’s a really strong sense of community. What’s great about the monastery to… not to jump around, or dodge the question, but I learned that community is so important. It’s just so important. 100 years ago, or not, even 100 years ago, 50 years ago, my father lived with three generations in one house. 

I think a lot of people from the early 1900 to 1930s lived that way. If there was a problem, they shared it collectively. If there was an illness in the family, they shared it collectively. 

Now with planes and everything… Look at us, we both said you live away from your parents. I live away from my parents, my brother lives in Colorado. Our brother lives in California. It’s very spread out. Our support system is scattered. Yes, we access them through Skype. We can access them through FaceTime and email. However, it’s a little bit of a different world.

Their support system is together. The responsibility of one becomes the responsibility of seven. 

If the toilet bowl breaks, seven people can fix it. The toilet bowl breaks, there’s no running water at my house, it’s my responsibility. The monastery, it’s shared seven ways. 

That leads to a really interesting and different existence. It takes a lot of pressure off you. You don’t want to let anyone down. For example, I’m cleaning the church, you better clean the bookshelf. It just leads to a really efficient system. 

Preston Pysh  36:44  

Jesse, talk to us about the Friday night hashing it out. What was it like 10 or 5 minutes that they had the opportunity to basically say their gripes to the community?

Jesse Itzler  36:54  

Yeah, every Friday night, they got together. It was sharing. They would just basically get anything off their chest or shoulders that happened during the week and put it to bed.

They didn’t walk around with resentment. They didn’t walk around harboring any kind of anger. They would just literally talk to each other, each of the brothers and each monk would get up… I didn’t share in this, this was their own private thing.

They told me that they would talk about anything that happened during the week that bothered them. They would discuss it and put it to bed. I thought,  “I want to do that with my wife because very often I won’t even say anything. I’m like, ‘You know what, I’m just going to let it go.'”

Then you let the next thing go. Then you start to have resentment. Then you get mad. Then you can’t go revisit it because it was a month ago, but it’s built up and it’s happened five times. 

I said to him,” Well, why do you guys do that?” He said, “Well, if I’m going to live with Brother Thomas, why would I not want to live in peace?”

If I’m committed to a marriage, why would I want it to be the best that it could be? Or if I have a relationship with my kids, why would I want to be the best it can be? So why would I tell my son, “Look, I’m disappointed in the way you did something, or I’m proud of this, or if it’s something I did that bothered you, tell me.”

It is so simple and obvious, but we don’t really do it. We don’t have a system to do it. Five minutes, once a week with my wife and we could say, “Did I do anything this week that pissed you off or did I do anything better?” It changes the whole relationship. 

Preston Pysh  38:26  

I think you said the magic word. It’s systematic. They’ve built this like almost a protocol into the way that they operate. I think that’s the thing that I’m taking away from the book, at least is to develop those protocols that really kind of optimize your life so you get everything that you want out of it.

Jesse Itzler  38:43  

Without question. We have mission statements for business. We write mission statements, but very few of us have our own personal mission statement. Very few people really write out like, “Well, what is my ideal day? What is my ideal life? What does it look like?”

If you were to script it, it probably wouldn’t be, “I want to see my parent and I’m not *inaudible*. I want to see my parents one time a year. I want to work 90 hours a week,” it just probably wouldn’t be like that. 

Little shifts can really make a big improvement, but it starts with an understanding of exactly what you just said. They wrote out and they chose the length they wanted to live. Theirs is one of simplicity. They map out the day, according to what that looks like. That’s a combination of social labor, community, meals, prayer and reflection.

It’s really like we all have those components in our life except our pie chart is a lot different. It’s a little out of balance in how it’s skewed. 

Theirs, to me, was a little bit more in balance of what I want now. I don’t want to go live in a monastery. One of my takeaways is I love my life. I don’t want their life but I want the components of their life to come into the way I live my life.

Stig Brodersen  40:04  

Jesse, what happened when you came back from the monastery, because I’m sure with all the time that you have, all the silence, and with all the good habits that you learned, what happens when you come home? People perhaps expect you to like to go into the same loop as you used to, but now you have all these new tools in your life that you would like to implement. How does the world react to that?

Jesse Itzler  40:32  

Well, it was hard for me coming back in, because remember, I came back into a world that hasn’t changed at all, but I come from a world that was completely different. Reentering was very difficult for a little bit of time. There was the transition period. 

However, here I am. A lot of time has passed and 90% of my life is back to where it was, but there are 10% of these kind of changes and things that you guys mentioned: listening more than talking, mapping out more of the lifestyle I want, spending five minutes a week with my wife, talking it out, having my own mission statement, having my own contract with myself of what my non-deliverables are. All that kind of stuff.

Also, being way more present and monotasking. I’m way more focused on it. It’s been way more efficient realizing that it’s okay to not… I can have a long to do list, but let me operate at a quality on the things that I’m doing. 

I started implementing a lot of the things that I learned. It’s been super helpful. Part of it for me was writing the book. It was a hard process. It took a really long time. It’s very different from the SEAL book, where there was one character. I had his voice.

In “Living with the Monks” there were multiple characters. There was a lot of silence. There was a lot of reflection. I wanted to write like a personal development book, but with a little bit of a different twist, a little bit of humor, a little bit of insight into a world, a spiritual world that not a lot of people have time or the ability to access. I want to share some of those takeaways with the reader so they could spend three or four hours in my book and not 15 days in a monastery.

Preston Pysh  42:18  

Jesse, I really liked this story. In the book, you said that you were there having dinner with some of the monks and you propose the question to them, “If you could have dinner with three people, who would they be?” Talk to us about the way that they reacted to your question and then tell us your story as well.

Jesse Itzler  42:37  

Yeah, I was at a dinner party before I went to the monastery. The host of the party asked everyone there to go around and meet three people that were alive, that they would want to have dinner with. It was a great exercise, but most of the answers were the obvious ones. Maybe Warren Buffett, Obama, Clinton or Oprah. 

When it came to me, all three of mine at the time, were truly rappers and the reason was I wanted to meet the three artists that changed the trajectory of my life as a kid growing up in New York. As a teenager, I want to thank them. I wanted to find out how they marketed themselves in an age of no internet and how they wrote their songs. 

After the dinner, I was like, “I’m going to invite the 10 most influential artists in my life to come to my house for dinner, and they all came.” People asked, “How’d you get them to come?” I was like, “I asked them.”

I only knew two of them, but I asked them in a very two way pitch. Most pitches are one way: you ask for something. It’s like a one way ask. I positioned it, which I think is very important how you position things, obviously, as an opportunity to almost like a summit over business ideas, how can we all help each other. You haven’t seen a lot of these guys in years. I’m putting this together for you guys, as much as it was for me. Then they all came.

I told the monks the story. The most were all religious figures, many of which I hadn’t heard of, but it’s a really good exercise to think about because we live in a world where you can have virtual mentors. Many of the people that I look up to I’ve never even met. I follow people on Instagram with just amazing stories and they’re just fascinating to follow. They are super inspiring and they don’t even know who I am, or we have no personal relationship. 

When you think about who are the people that are most like you in your world where you’d really want to spend time within? How do you get them? How do you get to know them?

Preston Pysh  44:38  

The reason I liked your response so much is because I think for a lot of people out there, they might answer that question by picking three people that could help them. That’s not what you did. You pick three people that you wanted to thank and show gratitude towards. I didn’t even read this in the book, but based on what you just said, and you wanted to help them in return.

Jesse Itzler  45:01  

I really did.

Preston Pysh  45:02  

That’s what’s so profound about your response. I think that’s why it resonated so well with the monks because there’s an undertone to your response there that I think is really deep and profound. 

For me, it’s the key ingredient, networking in general. I know that we’re kind of stepping into a different discussion there, but so many people want to network and they go about it in a manner like, “Hey, what can I take from you?  How can you help me?” That’s their pitch, right? 

Jesse Itzler  45:35  

You’re right. I have told that story a lot of times and I have never realized you’re right. I really did want to help them. I still do. I never really looked at it that way, but you’re 100% right. I really got them together. I wanted to offer something to them, but I was rewarded way more than them.

Preston Pysh  45:55  

It was your reciprocity, right? It was your way to give back because they gave you so much. I don’t know, I really liked that story. I think it just speaks so much on so many different levels. I thought it was such a good point in the book.

Stig Brodersen  46:07  

Jesse, the next question that we have for you is really something that we’ve been looking forward to because I think it’s evident for everyone listening to the show how much life experience you have. I also think how much you question common norms. 

We read this amazing book by Oprah Winfrey. It was a book called “What I Know for Sure.” The title really came from when she was a guest on a show. Then the host asked this profound question about what she knew for sure. She simply didn’t know how to answer it. 

My question to you is, like looking back on your life and also forward, luckily, what do you know for sure?

Jesse Itzler  46:50  

Oh, my gosh. I know for sure that one day my time’s going to run out. Like we said, I’m very aware of my relationship with time. I know for sure that I want to collect as many I want to build my life resume during my journey. I know for sure that that’s what makes me feel most alive. I know for sure that that will kind of extend my days and keeps me young. 

I know for sure that I want to spend as much time with the people I want to spend it with doing the things I want to do. That might not be every second of every day, but I am aware that that is the most important thing other than health to me right now.

Stig Brodersen  47:35  

Specifically about this experience living in the monastery, what can you take away from that you now know for sure that you didn’t before?

Jesse Itzler  47:45  

Really how important it is to spend time alone. For me, I’m not into meditation. I’m not against it. I love it. 

My form of meditation has been running alone. I ruun pretty much every day for 25 years, I’ve run 36,000 miles, 10,000 hours. That has kept me really in tune with my gut. I think just in today’s world, like constantly having my phone attached to my hand, it’s really important to spend time alone and keep that one superpower we all have that is free. That’s intuition. 

I think that the only way to exercise that muscle and have sharp good instincts and clarity is to spend some time alone and free up. Like we only have a limited amount of energy in our head and if it’s constantly bombarded and under attack… I think the average American makes like 35,000 decisions a day or something. When you free up some of those decisions, it gives you room to be creative. It gives you more energy to do tasks.

Preston Pysh  48:51  

Jesse, last question here. We know you always have something brewing in the background. We know you’re always up to something. So what is that something?

Jesse Itzler  49:04  

I have a great event. Stig, I got to get you to this one man. We’re doing an event again. We are doing Everest again. For anybody that wants an amazing challenge, come join me. Maybe Preston and Stig will come too. 

Similar to what we did in Vermont, where we rent a mountain, the entire mountain. You hike up and take the gondola down. We did that in Vermont and it was called 29029. You go up, gondola down, up, gondola down until you climb the equivalent of Everest. We’re doing another event. We’re doing that in October. 

We’re doing another one called Denali. It’s the equivalent of Mount Denali, the highest mountain in North America. We’re doing that in August at Snowbasin, a resort that we rented, a mountain we rented in Utah. We bring in tents and all this stuff. You have three days to do it so you can hike, walk, flee, hike, walk, sleep, but I love challenges like this because it really resets me. It really helps me. 

There’s an old Japanese ritual called the misogi. The notion around misogi is you do something so hard one time a year that the benefits last the entire year. I try to do one or two of those a year. This August and this October, we’ll be doing it again. It’s an amazing weekend. If anyone’s interested, I give a free shameless plug.

Preston Pysh  50:29  

We will link  it in the show notes too.

Jesse Itzler  50:31  

Thanks. Just go to JesseItzler.com and check out the experiences. We’d love to have you join me. Preston, we had an amazing time last time so hopefully. Stig, you’re more than welcome to come as my guest. We will summit talk. Enjoy the altitude.

Preston Pysh  50:52  

I’m debating on whether I bring my wife. That’s my question. It’s not whether I go. It’s whether I bring my wife because I think she wants to go.

Jesse Itzler  50:59  

I’m bringing my wife to both. Oh, and then I have this. You guys will love this so I’m turning 50 this year. You might have to get me on one more time and if I’m so lucky. I’m bringing in 50 experts and 50 things that I always wanted to learn how to do. It’s like once a week for the entire year to come to my house. I want to learn how to wakeboard, drive a stick shift, be a master at chess and play ping pong. This is unbelievable.

Preston Pysh  51:34  

This is the best part. It was like he completely forgot that that was something that was happening. Like he wasn’t even going to mention it on this show then brings it up. You’re out of control. I freaking love it. 

All right, Jesse. We’ll definitely take you up on that. We definitely need to talk about that in the future. We’ll have a link in the show notes to Jesse’s page there. Please click on it. I can tell you from firsthand personal experience doing the Everest climb was just epic. 

Leading up to the event for me, there was so much pain happening in my life during that period of time kind of just training for this, that when I did the event, the event was just incredible. 

Then when it was over, I had this setback in my life. I don’t know if I would call it a setback, but you should just feel like this energy loss. You know what I mean? Like there was just like this energy loss. It was so absolutely epic. There’s no other word for it. Check it out. J

Jesse Itzler  52:33  

Thank you guys so much. You guys have been great to me. I really appreciate it. Thanks and good luck with everything. Good luck with all the new ventures ahead and the podcast. Thanks for giving me this opportunity. It’s part of my process. I just really appreciate you guys. I’m not just saying that. I really do, so thank you for always helping me out. 

Stig Brodersen  52:56  

Alright guys, that was all that Preston and I had for this week’s episode of The Investor’s Podcast. We will see each other again next week.

Outro  53:03  

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