Jesse Itzler's Exact Playbook For Creating HIT AFTER HIT (#504)

Jesse Itzler

Go rent the countertops of all the liquor stores. Then go to Nabisco or one of the big boys and be like, "Hey, guess what? I own 10,000 countertops."

Jesse Itzler

You wanna put your widget there. You wanna put your **fucking** widget there. Keep the money watered on. Keep the money watered.

Sam Parr

Okay everyone, what's going on? This is Sam. We have Jesse Itzler on the pod today. He's a very fascinating guy who started a bunch of different companies, the biggest one being Marquis Jets. We got into some of the economics of that business, and he's done a lot of other things as well. You see him on social media; he's accomplished a lot. His life advice was actually really amazing. We went deep into some of the numbers behind his businesses and learned about his early career. There are a ton of takeaways. The pod was only supposed to be 60 minutes long, but Sean and I were so into it that we went over. I think we went for about 90 minutes or something like that because his story is super fascinating. If you liked the Rob Dyrdek episode, which a lot of people did—it's our most listened-to episode of all time—I think you're really going to like this one. It was pretty spectacular. I left feeling good about it. If you're watching this on YouTube, do me a favor: hit that subscribe button and make a comment. We've had a ton of people comment on our videos lately, and a lot of people have subscribed. We see the data behind it, so it's awesome that you guys are doing this, and it means a lot to us. We actually text each other all the time when someone makes a funny comment, so let us know! If you're listening on iTunes or Spotify, hit that download or subscribe button—whatever it is on those platforms—because we get notifications about those too. It's awesome! We're killing it, we're growing a ton, and we appreciate the army of people who are supporting us. Alright, enjoy the episode! Let us know in the YouTube comments what you think.

Shaan Puri

Alright, well, welcome! We got Jesse Itzler here, also known as, I think, he might be the richest runner and white rapper in the country. So, congratulations, my friend! We are excited to have you here.

Jesse Itzler

I love that! If you keep adding categories, I could be the richest in the world. If you start adding, like, you know, then have 4 kids that eat plant-based, etcetera, etcetera.

Shaan Puri

Right on! I'm excited to talk to you because you've done a bunch of amazing things. We've talked about you on the podcast, and we sort of spoke it into existence. I think we talked about it, and somebody might have sent you a clip. I'm not sure, but you reached out and said, "Hey, I'd love to come on." I'm just going to read a couple of these things to flatter you real quick, just so that the audience understands your background. So, like we said, you started out trying to make it as a rapper and ended up creating a jingles company. You were making jingles for sports teams, then ended up selling that. After that, you created Marquee Jets, a fractional jet ownership company, and sold that to Berkshire Hathaway, which Warren Buffett obviously runs and owns. You're married to Sara Blakely, the founder of Spanx, and you are an epic fitness athlete yourself—a prolific runner. I read your book, and the day I got really into you was when I read *Living with a Seal*, which is the story of you living with David Goggins for 30 days. I can't even really listen to David Goggins for 30 minutes on a podcast, so living with him for 30 days? Respect! You've created a bunch of companies outside of that, partnered with Zico Coconut Water, and are doing a bunch of prolific things. You have a very prolific career, but the start was like anybody's—it was humble beginnings. So, talk about the early days when you were trying to do the jingle company. You told me you were sleeping on couches at the time, trying to make it. Describe what was going on at that time in your life. What was the plan, and what were you going through? How did you come out of that? Well, I...

Jesse Itzler

I grew up in New York in the eighties when rap and hip hop were starting to emerge in a bigger way. That was the intersection of that happening and me going to college. I was really into music early on, and while all my friends in college were writing resumes and going on job interviews, I was like, "I'm making a rap record." Why would I waste my time making a resume? I wanted to make an album, so that was the direction I wanted to go in right away. I ended up signing with a record company called Delicious Vinyl. Everybody passed on me, and this one little record company gave me a shot. I didn't have connections; I didn't have a lawyer. I did it all myself. However, I ended up getting dropped from the label shortly after. Then, I got into writing jingles for companies and theme songs for sports teams. That was kind of my first entry into the industry. I pivoted because it didn't work out for me in the music business, but I still loved music, so I stayed in there and started doing jingles. Yeah, that's how I kind of started out early on.

Shaan Puri

You told me you were sleeping on couches, trying to make it. Then, somebody offered you a tempting deal. They said, "Yeah, I'll give you $10,000 if I can get 10% of everything you'll ever make." How did that happen, and what was your answer?

Jesse Itzler

Right, so I was writing theme songs for sports teams. I was 22 or 23 years old, and my business model was to write a song on spec and then cold call a professional sports team. I would try to get a meeting with them, convince them that they needed a theme song, and that was my business model. At the time, I was bouncing around from couch to couch. I wasn't homeless, but my friends were putting me up as I tried to figure out how to do it. I had just moved to New York from Los Angeles, and I had no money to go into the studio to write any more songs on spec. So, I needed money to fund that production. A music manager said, "You know, I believe in you. I'll give you $10 for 10%, but I want to own you for the rest of your life, basically 10% of anything you make." I was like, "I'll take it," because I needed the money. To me, it sounded like the deal of the century. You're going to give me $10, and all I'm going to do is pay you if I make it? That sounded amazing to me at the time. I was living on my friend Melissa Katz's couch. I met her actually at a bar, and she had given me her number on a napkin. She asked me where I lived, and I said, "As of Monday, I have nowhere to live." I was getting kicked out of my friend's house on Monday. She said, "If it's an emergency, you can come live with my roommate." On Monday, my friend kicked me out because his parents were coming for a week, and I thought, "This is an emergency." So, I was living at Melissa's house, and I told her about this opportunity. She said, "Well, why don't you go talk to my father before you give away 10% of your future earnings?" As it turned out, her father was a very successful entrepreneur. He owned a company called Kinney Parking, which operated parking garages in New York, and he was, I think, the second largest shareholder of the New York Yankees.

Shaan Puri

you're like melissa your apartment is really nice

Jesse Itzler

What was amazing about that was it really wasn't, and that's why I was taken aback. I knew her dad was an entrepreneur, but I didn't know the extent. By the way, his name is Luke Katz. He passed away a couple of years ago. He was an incredibly influential guy in my life, and this was my first encounter with him. I went to see him, and it's really relevant for anyone listening. What he said to me as a 22-year-old was profound. I told him my dilemma: "I'm going to take $10 for 10% of my life." He said to me, "Jesse, will you make this business work without the $10?" I replied, "Lou, I'm onto something. I know I can make it work." He took his notebook and literally threw it on the ground. He said, "I didn't ask you that. I didn't ask you if you can. I said, will you? There's a big difference between can and will. I know you can start a podcast. I know you can be a millionaire. I know you can run a marathon. I said, will you, son?" I said, "Yeah, will Lou, I will." He said, "Well, tell him to take the $10,000 and shove it up his ass. We'll make it work." And I did. It was a really powerful lesson. I signed up for this journey as an entrepreneur. Let me go figure it out. That's what I want to do. He breathed that flame into me at an early age, and it's really been a theme throughout my life in all the buckets of my life: the whole will versus can notion.

Shaan Puri

and why why is that so powerful the will versus can

Jesse Itzler

Well, because it really puts the pressure... You know, Billie Jean King in a book says, "Pressure's a privilege." And it is! As entrepreneurs, we play for pressure, Sean. That's what we want, man. I recently did a race called Ultraman. It's a 6.2-mile open water swim, a 265-mile bike ride, and a 52.4-mile run. I thought to myself before the race that exact thing: "I think I can do it, but I'm never gonna know unless I sign up for the race and put myself in a position where something incredible can happen... or not." But I gotta put myself in that situation. Now, it's up to me. Will I get it done? What am I willing to do? Am I willing to suffer for that one day to have the next three decades with that in my memory bank and on my resume? And I am willing to do that. And I did.

Shaan Puri

So, you know what's really funny? After you told me that, I did a call with you the other day just to prep for the podcast. I said, "Hey, you know, we're going to talk about this and this. Do you have any good stories?" You told me about this "will versus can" thing. The next day, my wife was literally like, "Hey, can you take out the trash?" I was like, "No, no, no, baby, it's not about..."

Sam Parr

can I take out trash

Shaan Puri

I will take out the trash, and she has no idea what I'm doing. I've been doing it all weekend. Once you see it, it's actually everywhere. Ben texted me this morning. He's like, "Hey, how'd you eat this weekend?" We're both on a fitness kick. He's like, "Can you stay locked in from now till Thanksgiving?" I just responded, "Oh, Ben, you're asking me? We don't ask 'can' questions anymore." As of meeting Jesse Itzler, I no longer ask "Can I?" It's "Will I or won't I?" That's it.

Jesse Itzler

Well, think about how many times in your life someone has said, "You, you, you!" You say something that you've done, like, "I did rim to rim," or "I climbed Kilimanjaro." You explain to someone, "Oh, I can do that," and in the back of your head, you're like, "Yeah, you probably can." But, you know, will you do it? There's just a huge difference between checking the box because you told yourself, "I can," versus actually going through and doing it.

Shaan Puri

By the way, Jesse, I have one other story that you don't know about. So, you used to go to something—at least you went once—called Coach K's Fantasy Camp, is that correct?

Jesse Itzler

I've been there for 18 straight years

Shaan Puri

Okay, okay, perfect! That's hilarious. So, you went to this thing. For those who don't know, Coach K was the greatest college basketball coach at Duke. I went to Duke, and my roommate Trevor used to volunteer at Coach K's fantasy camp. "Volunteer" was literally volunteering. I was like, "So what are you? You're staying over from break?" Because it's during some break. And he's like, "Yeah, I'm not going home. I'm gonna work this thing." I'm like, "Cool, how much are you getting paid?" He's like, "I don't think we really get paid, but you know, whatever." Like you just said, he put himself in a position for something good to happen. What I did, what he didn't know, and what I didn't know, was that the only people who go to this camp, which costs like $10 to attend, are basically like business ballers trying to live out their dream of, "Oh, as if I was an athlete." So, all he was doing was driving the shuttle back and forth between where y'all were staying and the event. He's like, "Dude, it's amazing! Just hearing these conversations, what they're talking about in this like 9-minute shuttle ride." Every night, he would debrief with me about ideas that he heard. He'd say, "Oh, this guy said that he does this, this thing over here. This guy said he does this." He told me, "I met this guy, super charismatic. I loved this guy's energy. He tipped me $100 for this like 10-minute shuttle ride." Later, I told him I was mentioning to you that you're coming on the podcast. He goes, "That was the guy who tipped me!" So, I don't know if you remember this or not, but we took that tip, and we had a business idea at the time. We needed to convince this famous chef in LA to come fly out and partner with us. We had no money. So, you and a little side job that I had became the money we used to pay for the ticket to fly that guy out, which definitely changed the trajectory of our lives. So, little did...

Jesse Itzler

you know

Jesse Itzler

I love that! I've been going there since I was 35. It's for guys 35 and older, and it's not to chase some crazy dream. It's a combination of meeting amazing people and also realizing that there's not a lot of time. I'm 55, so I'm older than you guys, and I can't stop that clock. You know, time's undefeated; it's always ticking. It's the 6 days a year, or the 5 days I go there, that I get to feel like an 8-year-old again. It's really one of the few times in my life that I get that chance, and I love it.

Sam Parr

I don't know man I follow you on instagram it seems like you live like an 8 year old a lot of times

Jesse Itzler

I'm pretty

Sam Parr

sure I just

Jesse Itzler

I had

Jesse Itzler

a lot I do I do I do

Sam Parr

I do

Jesse Itzler

I shouldn't say that

Sam Parr

I'm pretty sure I just saw you in an RV with like eight friends, just running around the country. It seems like you have the eight-year-old life kind of nailed down.

Jesse Itzler

I like to give myself that excuse, Sam. I guess you’re right; it’s more than once, more than five days a year.

Sam Parr

Yeah, I think you've done that alright. And then, was your first kind of major business Marquee Jet? So, did you go from jingles to jets?

Jesse Itzler

Yeah, so interestingly, I had... the jingle thing turned into a real business. I found an opportunity. I started out doing jingles just for anyone that would pay me anything to do anything. So, I was doing jingles for, like, honestly, Turbo Bubble Gum, this bubble gum company that no one ever heard of. Like, just anything that you...

Jesse Itzler

paying me

Shaan Puri

intro needs a little sprucing up if you wanna if you wanna dust it off yeah

Jesse Itzler

I I I got you guys and and then I start and then one of those jingles gave me an opportunity to write a theme song for the new york knicks I had done a a commercial a radio ad for a company called in the in the pain clothing it was owned by nancy grunfeld ernie grunfeld the gm of the knicks' wife and she really liked what we had what I had done and she said yeah if you have any other ideas you know let me know I said well I'd love to do something for the knicks you know like write a theme song and we can shoot a video they can sing it in the arena so I approached the knicks to do this song called go new york go and the knicks paid me $4,000 to buy the song outright I'll never forget it like I actually borrowed money to go in the studio to do this to do the song I didn't have enough money to go in the studio to record it because they were paying me 30 or 60 days later and by the time I paid the studio the engineer the lawyer that I had the singer the producer it cost me $4,800 to actually deliver the song that they were paying me $4,000 for and when I look back on it you know for most people they would be like that's a terrible business model it was the best business model in the world for me because when you start out you know people buy into stories momentum and people very often more than the products like I was the business plan and I would have paid the knicks $10 to say they were my customer because once I had the knicks those phone calls to get onto the other sports teams became very easy and that became my calling card so I built a business around that sean that actually I I ended up doing theme songs for almost every professional sports team and turned it into a business where we were selling cds like this I would take the songs they play in the arena add my original song with great moments in the team history and sell them at retail I sold that company to a public company called sfx and that was my first I was 27 we sold it for $4,000,000 and then we had there was an earnout for another 12 or 16 or something which we earned out and that was my first kind of like get off the couch moment I was no longer on melissa's couch and I moved into my own space

Sam Parr

what was your take home after that

Jesse Itzler

I had a partner, and at the end of the day, I think on the first $4,000,000, I made like $1,500,000. By the way, $1,500,000 to me...

Shaan Puri

all the money

Jesse Itzler

I was Elon Musk before Musk was born. I was walking around like I was Musk. I had a million and a half dollars. I would wake up at 8 and go to the ATM. I would get my printout of my balance. I swear to God, then I would wake up the next morning and be like, "Are you fucking kidding me? I have $300 more than I had yesterday and I was sleeping!" I'm like, I'm going...

Shaan Puri

back

Jesse Itzler

to bed

Jesse Itzler

I'll go back to bed stop making me have the money in bed

Jesse Itzler

My partner convinced me to take all **$1,300,000** that we both cleared after taxes, or whatever it was, and reinvest it to get exclusive deals. We made the business bigger and got our earn-out. Then everything changed a little bit for me. But, you know, I had no idea how to manage money. My parents never talked about money. My dad owned a plumbing supply house, and my mom raised four kids. The thing is, I had no relationship with money. That might sound weird, but people talk about relationships in terms of their relationship with their kids or their significant other, but not in terms of their relationship with time, which is very important, and your relationship with money, which is equally as important. I had no relationship with money, so when I got money, I didn't know how to save it, how to spend it, how to use it, or how to act around it. I was very immature around new money, and you know what happened to me? I lost it because I didn't know anything about it. Fortunately, I was able to bounce back through having other successful businesses and failures, but no one ever told me about it.

Shaan Puri

how'd you lose it just overspending or what'd you do

Jesse Itzler

Overspending, thinking like, "Oh, that was pretty easy. Man, I could just do that again," you know?

Sam Parr

what did you buy

Jesse Itzler

It wasn't so much what I bought; it was just, you know, helping my parents and spreading it out. I wasn't abusive with it, but I just didn't know how to really handle that.

Sam Parr

That's pretty common, right? Like, you know, Sean and I have a bunch of friends who are both about 34 or 35. We have a bunch of friends, and ourselves as well, who had access at a young age. The thing about selling a company is that it's different. There are usually two types of people I've noticed: people who have cash flow businesses, or they're like a lawyer or something like that, running a law firm. Their income is going up a nice amount every year, and you get used to having that cash flow. Then, the other group of people are typically young folks who sell their company. Typically, those people are like me. I paid myself $20,000 in year one, $20,000 in year two, and then $50,000 in year three. Then, I sell it and make a lot of money, and you're like, "This is just overwhelming. I don't know what to do with this." Yeah, that's a pretty common thing. I don't think most people blow it, but I think it takes about two or three years to accumulate, get used to it, and learn what to do. But there's no one to teach you.

Jesse Itzler

The problem is I had always been taught, "Oh, if you're a millionaire..."

Sam Parr

the shit

Jesse Itzler

Was the no? But I've been taught the opposite. If I saw a millionaire, that was like the pinnacle. Like, he's a millionaire, man. So I always thought, "Oh, I have $1,000,000. That's all I need to have for the rest of my life. I'm a millionaire at 27." And that was the relationship that was wrong.

Sam Parr

right yeah you could spend that you could spend that easy

Jesse Itzler

Yeah, you go on and you have a $4,000 dinner when you were eating, when I was basically eating a 99¢ bagel for 17 years. You know, things change quick.

Shaan Puri

I'm a big believer that most of life, most of your life, is a result of the conversation you have with yourself in your head. Do you remember after you kind of had that first hit and you see the money? You're only 27, and you still have all your life ahead of you. Do you at all remember the conversation you had with yourself? Like, "Alright, Jesse, so now..." Whether "now" was a good conversation with yourself or a misleading one, do you remember what the conversation you had with yourself at that time was?

Jesse Itzler

you know it was interesting because shut I was living in new york and most of my friends were working on wall street they were working at hedge funds they were making they were making a lot of money there was a lot of money around me and you know it's very easy to get caught up in what's he making versus what am I making and it's very easy to like you start having those conversations with your yourself you can go down and spiral downward very quickly and you know what I was making well it took me years to make and build and sell and my journey to get to that. Was crazy I was selling carrot and celery sticks door to door that didn't work I had a t shirt company that didn't work I got dropped from a record label that didn't work I saw I cleaned meat traps that didn't work I sold chicken shrimp and meat door to door that didn't work I mean jingle company I it went on and on so you know I had really worked so hard and and at the same time like I invested so much not for the money but just like I just wanted to get a record deal man I didn't care about the money I just want everyone said you can't do it everybody and it was it was such a driver if I remember I listened to a podcast where one of you guys were with laird hamilton and you were saying how that he was saying how that you know one of you guys was saying you need that anger to inspire you like some kind of fuel you know so I had that I still have that don't get me wrong I still have that and I never want to lose that underdog mentality I never want to be like I'm at the top of the mountain I'm not I consider myself back of the pack everything back of the pack sales back of the pack entrepreneur there's so many better entrepreneurs than me so many better salesman than me but I I but I love that feeling of I gotta prove myself so when the money happened it was just like oh steve stark is making so much more than me we're in the same basketball run like I gotta catch stark you you know

Sam Parr

The Marquis Jet thing is interesting, though, because that's like totally out of left field. That seems like a way bigger win than the jingle business.

Shaan Puri

same partner right same same cofounder

Jesse Itzler

yeah same partner it was a much bigger win and it what like most things in my life they most of the businesses that have that I've been involved with weren't planned you know and most of my successes in life haven't been in my business plan they've been opportunities that presented themselves you know my whole life I've been taught when opportunity knocks you know and I'm not I don't wanna sit around waiting for opportunity to knock I like to create my own my own opportunity and I was a guest on a private jet with my partner and I was like people fly like what is this what is this that I'm on and we it led to some research like there's only really 2 or 3 ways to fly privately back in the nineties when we started marquis jet you can buy your own airplane if you had $50,000,000 you know or something like that well that's out of the question you could get a fractional be in a fractional program like netjets but even that is a really big commitment both in capital and time it's a 5 year commitment a lot of money up front that wasn't I mean that wasn't an option for us or you could charter and there were a lot of questions around well who owns the plane who are the pilots you know do I feel comfortable on that what if the plane doesn't show up so we found a little white space there and said you know we only want to fly like 25 hours a year and I bet there's a lot of people like us that don't wanna own an airplane don't want the responsibility but they just wanna be able to have the have a plane available on short notice and that was the idea around selling a 25 hour jet card that would work like a debit card so if you and if you and samsung flew 2 hours you'd have 23 hours left and then we partnered with netjet again part of being an entrepreneur is figuring out how to get from a to b the fastest and for us for me in my life many times it's been through partnership we partnered with netjets they ended up buying us to use their airplanes partnered with coca cola at zico at zico colton auto they ended up buying us so but anyway that was that's what happened we were a guest on the plane and you know walking around eyes wide open looking for opportunities and said wow this could be really interesting and and then started the journey of figuring out how we could pull this off because we had no aviation experience very little money and you know I was younger than you guys I was 28 29 years old and figuring out like man we need a lot of airplanes where do we go for airplanes and and then started that journey of of building this company

Shaan Puri

So, you walk in. You walk into NetJets and you're like, "Hey, I'm Jesse, former rapper, jingle preneur, and I would like for you to give me your most valuable assets, your planes, for this new membership program." How did you convince them to do that?

Jesse Itzler

well at first we didn't they kicked us out of the office in the first meeting after about 12 minutes and backing that up the bigger question is how we even get in the room forget like what happened at the meeting how in the world did a multibillion dollar company let 2 kids that didn't break a 1,000 on their sats into a room to pitch them the idea a year before that I was a yes guy my whole life I I was I I've I've kind of and I still try to pride myself when people ask me for things to deliver if I can but never ask for anything in return you know like I'm not like oh stan I'll do this for you sean but like can you do this from like I don't know that's not bmo I got a call a year before that from someone that said that their daughter this is a true story and it's the craziest story ever this guy was having a his daughter was having a sweet 16 and a famous singer was performing in his hometown his daughter wanted to bring his sweet 16 to the event the guy says I know you know the manager can you help this guy get some tickets and do anything special turns out I get the guy's daughter as a backup singer for one song with the mic off everyone at school the next day is she's like the hero of this like what happened oh my god they're freaking out the guy calls me up he goes I don't know who you are I don't know what you have what you do but you lit my daughter up and if you ever need anything let me know like turns out he I can't make this up he's the president of that jets a year later I need 650 airplanes like oh no I'm like jim you're never gonna believe this the the guy you've got your daughter on I have an idea for a thing he gets to me the meeting we get thrown out of a meeting 12 minutes in because they're like we're not giving 2 kids access to our 650 airplanes and this guy jim jacobs comes up to me after the meeting he goes you know what that was amazing I said we got thrown out in 12 minutes what do you mean a meeting he goes rich santulli my party he doesn't give anyone 12 minutes he goes this is not that he'd come back next week and bring this thing to life repitch it I need more information so we came back the next week and we realized we can never sell them in a powerpoint which is like what every guy sees a 100 powerpoints every year we brought in our own focus group we had 8 people in the lobby and they walked in 1 by 1 and they stood up and said that they would never buy a fraction of an airplane what netjets was selling but they would buy a 25 hour jetcard and at the end of the meeting they literally said if you guys raise money or put up your own money if you can figure it out we'll give you a shot and a couple of years later we had more customers than that yet

Sam Parr

that's crazy

Shaan Puri

You showed him the market. You were like, "I could either put up a chart or a pie chart right here, or I could literally walk the market into the room and have them say, 'I need this product.'" It turns out that eight people saying, "I need this product," to your face makes a bigger impact than a pie chart that says 11% of the market needs this.

Jesse Itzler

when I think back on this moment at 28 years old and we had like carl banks from the new york giants I think run from run dmc was there he was right behind me on the wall you know when these guys that meeting yeah we brought we brought him in we brought him in and when we said when when when we they got up 1 by 1 and explained why this card would work and you know I think what they realized was they had been pitching to a much older corporate client and that they what they realized I think in the meeting was here are these 227 year old kids and by the way remember I said people buy into people's stories and momentum this had nothing to do with our product the decision maker looked us in the eye and said I see enthusiasm I see someone that's no matter what even though they have no aviation experience is gonna make this work and I'm willing to bet on these 2 guys it wasn't there was no powerpoint it was us like you're the business plan you are the business plan so at the end of the meeting he literally said to us after we got the deal in you know like year 1 we did a I think we did like close to 200,000,000 in sales year 1 and I remember going into his office and and asking I said rich santulli who is like united me man united me I said rich how do we how do we end up here man and he looked me dead in the eye and he goes you guys remind me of me when I was 27 and bringing in this focus group yes they came in and they explained why they would buy a card and yes they saw a much younger demo that someone could be a lifetime customer now at 25 versus a lifetime customer at 50 so they saw the lifetime value of what we were bringing in this younger generation of athlete entertainer you know young mogul etcetera that they wanted that because that's incredibly valuable to get that person on their plane at a young age but at the end of the day they he saw something in my penny and I my partner and I that he wanted to bet on and you know I just want to say this for anyone listening here because I know this is primarily a business podcast by the way it took me 37 minutes to warm up but now I'm fully here he's here I'm slow I'm slow today but I got it now you know like I said that was never in our business plan oh we're gonna bring it on focus group to start a company that does 5,000,000,000 in sales it's like it's the things that live off the the business plan that make the biggest difference and when you have a chance you you know you don't get a lot of big meetings like that and I remember at 27 walking in there and saying to my partner like this is as big as it gets because you know what there is no one else that has 650 airplanes this is it and you have to bring that meeting to life you have to stand out you have to you know not in a gimmicky way but you have to make that memorable man and and fortunately we were able to do that and it worked and then we had an amazing amazingly fruitful relationship and partnership with netjets until we exited

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Sam Parr

Alright everyone, a quick break. You're listening to this episode. You've maybe listened to a bunch of MFM episodes. We get a lot of interesting insights, and the reason we get insights is that I have a lot of peers and friends who are CEOs of companies. I'm able to ask them all types of different questions. It all started because I used to run this event called HustleCon. I would convince these speakers from big startups—you've probably heard of most of these companies, like the founder of Grammarly, WeWork, Away Travel, Casper—all these cool companies. I would sit in the green room with them and hear all these amazing stories. But I would also learn how to fire someone effectively, how to handle things when the business isn't going well, and how to manage situations when it's going great. All these things happen behind closed doors, and it changed my life. So, I started this company called Hampton. JoinHampton.com is the URL where we make it really easy to have a peer group and a network of other entrepreneurs who are like you—similar industries, similar-sized companies. If you run a company, check it out. The average company is doing about $25 million in revenue. Some companies go all the way up to $200, $300, or $400 million in revenue and are publicly traded. Others are a little bit smaller, in the $1 million to $4 million range. My partner and I, Joe, review every single interview. We hand curate and hand select all these interesting people, so it's been a really wonderful community. If you want to be a little less lonely and find information and insights that you can't Google, check it out. It's Hampton—that's the name of the company—and JoinHampton.com is the URL. So you should check it out. I review all the interviews, so enjoy the rest of the episode. Are you... so, like, I think that all three of us might be a bit similar in business relationships, where we bring the passion and some of the creativity and the 0 to 1 stuff. Were you good at running that company, or did you have a good partner who was running it while you were great at bringing some of the deals to fruition?

Jesse Itzler

I can only run marathons; I can't run any business. I'm not good at running anything. No, I'm a terrible operator. I'm a terrible manager. But I'm really good at knowing that I'm terrible at that and being okay with it. So, you know, we were able to hire a CEO right away, which allowed me to focus on sales, something I was better at. Buzz, which I was really good at before Instagram. I'm not so good at it now with Instagram, but back when there was no Instagram, I was good at creating PR-able opportunities and talk-worthy events. For my year, that was really important. So, no, I have never been the CEO of a business. I've never run or operated a business, but I've been a founder five times.

Sam Parr

And how does that model work? Is it like a Costco model where you were breaking even on the $200,000,000 in sales, but you made money off the membership?

Jesse Itzler

No, so the original deal with NetJets was that we were leasing time on their planes. But I wouldn't have to... we wouldn't have to enter into a long-term lease until we sold this. We had no risk; they were carrying all the paper. So if I bought... if you and Sam, Sean, you guys bought 100 hours, we'd go buy 100 hours, and it was marked up. We were just a marketing organization. They owned and operated the planes, and we were leasing it. As we got big, all of a sudden we had 4,000 members and were doing $1,000,000,000 a year. Then the model changed, and we had to start buying our airplanes. But by that time, we had significant cash, and we were able to do that. So it started off with... literally, it was an incredible deal for us and for them. It was a true no-lose for both parties.

Shaan Puri

And those headline numbers are really big. How big was that exit? I mean, that's a pretty big thing. How big is NetJets? I don't even know.

Jesse Itzler

I don't even remember what netjets sold to berkshire for I'm sure it's public

Shaan Puri

this was before berkshire owned it is that right

Jesse Itzler

NetJets sold it to Berkshire prior to us. Okay, and then we went to... now we're part of NetJets. Just which is your Berkshire stock.

Shaan Puri

because that would have been a good stock to just get in the deal

Jesse Itzler

I know right no we didn't

Sam Parr

NetJets sold for $725,000,000, and half of it was paid in stock. So that was, if that was a good deal for NetJets, depending on... I don't know what the revenue was, but that's a lot of money.

Shaan Puri

You snapped your fingers and you were like, "We did, first year, we did whatever." I forgot what you said, $200,000,000 or something.

Sam Parr

200 I

Shaan Puri

don't know what that means what what is 200,000,000 there that that's not that can't be membership dues that's that would be

Jesse Itzler

Insane, no it is. Yeah, no, because our average customer spent close to, I think it was $250,000 or $235,000 a year. Gotcha, okay, but it...

Shaan Puri

Is more like a GMV. So, because you have to... your take is some spread between that and then whatever it matches. Okay, gotcha.

Sam Parr

So, yeah, I guess like on that model, what's the income on $200? Let's just say $100,000,000. What can your profit be on that?

Jesse Itzler

Well, this was 30 years ago, so I don't remember exactly what it was. But it was enough that I was now off the couch and living a very good life. By the way, the best ROI in that deal is that I met my wife there. She was a customer of ours, and that's how I met my wife.

Shaan Puri

You told me something about getting the first customer. So, before your wife was even a customer, you were on this plane thinking, "Holy shit, this is an amazing way to fly! I'd love to do this. I'm sure other people would love to do this too." You came up with the idea, which is cool. Now, how do you go get those first people to give you $200,000 to be a part of this? That's a huge question. Where did you go to find those customers? Can you tell the story of how you got it off the ground?

Jesse Itzler

Well, we started out, you know, I think the first thing that any entrepreneur, at least in our position at Mark Kichard, had to establish was credibility. Because if I was going to sell you time on a plane and you said, "Who flies with you guys?" that would be my first question, or one of them. If I said, "Oh, my dad and my next-door neighbor," you probably would leave. But if I said, "You know, Oprah, Bill Clinton," you'd be like, "Wow, they must have vetted this." So we started out looking for athletes, entertainers, and high-profile people, which was not easy for me. But I had to go where wealthy people congregated. I heard about this conference in Monterey, California, that was just getting some traction called TED.

Sam Parr

so I

Jesse Itzler

I flew out to Monterrey, and you know, I told the guys, "Hey, I'm going to get my first sale. I'm going to this thing called the TED Talk." They were like, "What?"

Jesse Itzler

no it's ted

Jesse Itzler

And it's in Monterey, California. You gotta like... you can't even get there. I connected through Chicago, rented a car, and drove 5 hours to Monterey. I get to the TED conference, and it's like Fort Knox, man. Everybody has a credential, like this huge badge. I'm thinking, "You need a credential to get in here?" There are no credentials to be found. So I'm plotting, like, how am I gonna sneak in? Should I buy someone's pass? I want to go into the room where all the qualified leads are. I'm in this coffee shop plotting my entrance. Every two hours, a wave of people comes in, and they're buying these credentials. I'm like, "Oh, this is where they come on their break." They're all buying lattes and muffins. So the next morning, I got up at 5 and bought all the muffins. I controlled all the muffin inventory in Monterey, California. I literally just waited. And this is a true story, by the way. It's been verified. So, two hours later, the first wave of people on their break walks in. A guy orders a latte and a muffin. I stop him and overhear that they could give him a latte, but they're all out of muffins. It's like... it's 9 in the morning, and they're out of muffins! The guy starts walking away, and I stop him. I say, "Sorry, I overheard you. I actually have an extra muffin if you want it." He's like, "You got an extra muffin?" I'm thinking, "I got every single muffin under the table, man. What do you need?" I started talking to him. He says, "What do you do?" I tell him what I do, and he says, "You gotta be kidding me! I'm in the market for a private jet card." His name was Josh Koppelman, and he owned a company called Half.com.

Sam Parr

famous vc right that was amazing now he is

Jesse Itzler

I bumped into him about three years ago at a retreat, and we were talking about this. Anyway, he was my first sale. That is not a story of me being a good sales rep because, like I said, I am truly back of the pack. But it is an example of me putting myself in a situation—will versus can—of putting myself in a situation where I could attract that kind of luck. You know, he was my first sale, though, Sean, to answer your question. And you know what happened after that? I'm going to tell you what happened after that. I serviced the hell out of him. I did what everybody listening would do, but I did 30% more. So when he went to Mexico, he expected me to return his call and the every DM and all that. Of course, I did what everyone here would do. But he went to Mexico, and he didn't expect a list of pediatricians that I vetted in case his kids got sick. He didn't expect me to make reservations every Wednesday night at 8 o'clock during spring break in Mexico in case he and his wife wanted to go to dinner. After a couple of months of doing that, what he didn't expect me to do was give him the magic word: a referral. That was rinse and repeat for five years until we grew this. So no, I was never the CEO. I was never the operator. I was never the COO. I wasn't even on the org chart.

Sam Parr

So, I'm looking at your website. Check this out! I use the web archive, and I'm looking at the 2005 version of MarkeyJet.com. I'm looking at your "About" page, and what's interesting is that your senior executive team was not only awesome, it was amazing! Because Ken Austin, I see, was your Executive VP. Is that the same Ken Austin who went and started, is it Avion, the tequila company? And most recently, started Proper 12 with Conor McGregor? Is that the same Ken Austin?

Jesse Itzler

and the tequila company with the rock yes

Sam Parr

you've done a good job of hiring

Jesse Itzler

No, we were the Boston Celtics, man. We were the Boston Celtics. From like the old... we had exceptional talent at this company. Ken Austin is exceptionally talented. I don't know, he could be... he is such a talented guy, and I learned so much from Ken. We had great sales reps, and we attracted really good talent because we built a really good culture.

Sam Parr

Well, it's also a sick product. I mean, you said you met your wife there. It's like, that's the greatest line ever! Like, "Oh, you're here at this jet company, so I know you're someone interesting."

Jesse Itzler

definitely

Sam Parr

Just so happens I work here, or I own the company. I mean, it's a pretty wonderful experience, I imagine, to work at a private jet company.

Jesse Itzler

It really was, and you nailed it. But the only thing I would say to that is, I think there were like 65 private jet companies that put a flag in the ground from when we started to when we sold. I think we were the only one that made money. I might be wrong about that, but it was something that...

Shaan Puri

Including Garrett Camp, the guy from Uber. He created an "Uber for jets," but that didn't work out, right?

Jesse Itzler

It's very, very difficult. If we didn't have NetJets as a partner, you know, it wouldn't have... I'm sure it wouldn't have worked as well. A lot of things lined up for us.

Shaan Puri

The business you did a partnership on was Zico Coconut Water. I think this is interesting because now we're seeing a pattern. The first is you're picking businesses in categories that they're not in the NBA curriculum. Nobody's thinking about, "Oh, sports teams need slogans and CDs that will increase their fandom." Nobody even realizes that that's a niche you can go into. Or to do, you know, this membership model for private jets. Nobody's even looking in that area at the time, right? There are very few people who are even thinking about that niche. It's not common. Then you go to coconut water. Now you're in consumer packaged goods in a beverage category that's nonexistent really at the time. I think Zico was pretty small when you found it. It's not like it had tons of momentum. So talk about two things: 1. Finding these niches. What is your operating philosophy that seems to consistently lead you to these? 2. The key partnership that got it off the ground. I heard an amazing Matt Damon story, and I want to hear the full version of it.

Jesse Itzler

what was zeek up yeah yeah I spent a year trying to figure out how to have my own coconut water company I went to brazil I went to jamaica look try to figure out this is there were no there was no coconut water in the store at the time this is I'm a so let me back it up even further I was running a 100 mile race and I did a lot of trick when I was doing my training I did a lot of research around hydration and nutrition if I'm gonna run for arguably 24 hours how many calories do I need to eat and drink an hour how many calories do I need to take in an hour how much fluid ounces do I need to drink an hour how much salt do I need an hour and my research led me to coconut water so I ran this race powered by coconut water and I finished it in 22 hours and 30 minutes when I was done I'm like this is gonna be this is the new gatorade no one knows about this I'm the human guinea pig I'm bringing this to market you know it's a better option it's all natural one ingredient you know it rains god sends it up a tree we crack it open and we drink it like this is I mean are you kidding me so I spent a year trying to figure it out how to import it and I realized like I did get an I eighty on my sat because I couldn't figure it out but I knew I could market and sell it I knew I could so again same model same formula I took it the idea to coca cola the president of coke's emerging brands division was friends with one of my customers at marquis jack he got me a meeting I pitched the meeting in the meeting I pitched this idea of coconut water he takes the liking to me but he says we don't buy powerpoints or coca cola we buy brands he goes but if you partner with another company or something you know maybe we can that that's out there that has proved that they can make the product ship the product get it in stores or whatever we'll come and we'll partner with you so I went to zico and that's how we formed the partnership during the meeting the about a week before I was at matt damon's house and matt was also a customer of a marquis jet and I did the things that I did for josh koppelman with matt and we became friends and I said to matt you know he'd asked me if I wanted to spend the night they were going out and I said I'm going to brazil in a day or 2 I can't see he goes what are you doing in brazil I said I'm starting a coconut water business he's like you gotta be kidding me he's like I love coconut I have a coconut tree in my backyard he's like I drink he goes if anything happens what you know with this company let me know I may wanna get involved a month later in the meeting at coke like the meeting is going so bad I'm showing him this powerpoint you know like and and out of nowhere I I know I had achieved the whole energy feel of the meeting I just turned to the president of the guy at cook and I'm like you know my partner matt damon and I and the guy went matt damon is your partner I said I didn't mention that

Jesse Itzler

what are you talking about

Jesse Itzler

We go all the way to the one-yard line. I leave and I call Matt. I'm like, "Matt, I need a favor." He's like, "What?" I'm like, "Can I come over? Can we climb up your tree, get a coconut, chop it open, you know, go in the kitchen, put a straw in it, and then turn to the camera and say, 'Mutar, mutar, Kent, the CEO of Coke, there's gotta be a better way than this?'" He's like, "Alright." I filmed this. He filmed this award-winning, frigging 35-second short film of him getting a coconut, chopping it open, and saying, "There's gotta be a better way." And we got the deal. You know what's interesting about that is, obviously, who's gonna get a megastar to come? That's not the... It goes back to what I said: will you make it work? Putting yourself in a situation where you can get lucky. Here's the other pattern, Sean. You're talking about patterns and making yourself stand out and be memorable in a meeting. Now, I stretched it a little with this one, but it ended up working out.

Shaan Puri

that's an amazing story that's amazing

Sam Parr

that's a good one

Shaan Puri

I love that story I love that story you

Sam Parr

that's wild

Jesse Itzler

I like coke bought it 2 years later 100%

Shaan Puri

Did you, when you bought, buy into Zico at the time? Was that like a "yeah"? And have you made financial bets that you felt were risky? You know, Elon does this thing where he sort of rolls all the proceeds into the next business and goes all in each time, which is probably not advisable to most. But what's your strategy been now that you have some chips to play with? Do you make big financial bets, or are you saying, "No, I'm going to add value strategically"? Do you start things from scratch? What do you like to do with the chips as you accumulate them? How have you used that to your advantage?

Jesse Itzler

Well, I've realized that as I've gotten older, more isn't better; **better's better**. I really don't make a lot of bets. I have four kids, and what I'm most proud of, Sean, in my journey at 55, is that I've exited five businesses, but I've been able to build a family, keep my health, and be a really good son to my parents. I have great friends. So, I really aren't... I'm not using Eli as an example; you brought him up, not me. But I'm not trying to roll everything in. I'm really proud of what I've been able to do, and I'm really proud of the life that I've built. I have this thing in my life: if it's high aggravation for high reward, I'm not doing it. That goes for anything—money, friends. I don't want high-aggravating friends. I'm on friend reduction right now. I want low aggravation.

Shaan Puri

Doing layoffs, you do Zoom calls with people to let them know, "Hey, I'm sorry we had to make a reduction in friendship."

Jesse Itzler

listen man we're doing layoffs man

Sam Parr

excuse me mister david can you step out of

Shaan Puri

My office, there's a severance package. We'll hit it three more times, but then that's it.

Sam Parr

we need to have a discussion

Jesse Itzler

That's great! That's so funny. But I'm not trying to, you know, push you really. It's based on my enthusiasm for something. How is it going to impact my life? Meaning, like day to day. I walked away from several ideas that I think could be really good because, just because you have a good idea doesn't mean you should do it. Sarah said that to me. I had an idea, and now I see people doing it. About 8 years ago, I said to Sarah, "I have an idea that's bigger than Marquee Jet." Marquee Jet was the biggest thing I'd done, you know? I walked her through it, and she goes, "That's an incredible idea. Don't do it."

Sam Parr

what was it

Jesse Itzler

I wanted to take this back eight years ago. Now it might sound like, "Oh, well, people are doing it now." I actually pitched this to a major airline that is now doing it. I wanted to make commercial travel feel like private travel for people. I felt like there was, and still is, an opportunity for people who would pay to fly commercial but want an experience that's more private. For example, if I'm flying from New York to California and I'm by myself on a Global or a Gulfstream, that's an expensive flight. That is an expensive flight! I could just buy a first-class ticket for maybe $1,500. So instead of, let's say, that flight costing me—if you charter it—maybe it's going to cost you, let's just say, $50,000. It might be more; I don't even know today what it is. But I could spend $50,000 on a private flight, which is amazing, or I could buy a first-class ticket for $1,500. As a $1,500 ticket holder, I would gladly give you another $1,500 to United, American, Delta, Frontier, or whoever, if you could walk me through a back door and make me feel like Mick Jagger, escorting me onto the airplane through the back door. No one was doing it. No one was doing it, and now they are doing stuff like that.

Shaan Puri

That's smart. It's like you unbundled the private experience. It's like, okay, there's the jet part of it, but then there's the right to walk onto the plane and walk off the plane.

Jesse Itzler

you be like okay because then what's you doing on an airplane do you really care what's you gonna do yeah

Sam Parr

it doesn't matter

Jesse Itzler

I'm in 1 a

Jesse Itzler

no one's bothering me in 1 a

Sam Parr

And in some regard, the commercial jet is safer. You have more amenities. So, yeah, like I... I flew first class from New York to LA one time for a meeting. I had never flown first class before, but I did it because it was overnight and I had to be ready for a meeting. I get on, and 1A and 1B are sitting right next to me with Stephen A. Smith. I was like, "How the heck did you get on the plane before me?" I looked it up, and apparently, there is like a private door, I guess, if you're famous. What is that?

Jesse Itzler

Well, I think now several airlines have it, and there are services that do it outside of the airlines as independent services. So, I had the idea, but I also felt like I had the buy side that I could deliver to the airline. You know, I'm involved with some NBA players, and I'm part owner of the Atlanta Hawks. I have friends who are all doing really well, and I thought we would want to have this service. So, I had the idea and a significant part of the buy side to package together for an airline to bring private flyers onto their mothership, which is the domestic part of their travel. But anyway, to answer your question, things like that are good ideas and lucrative. But for me, at that point in my life, I feel that I don't know if I have the energy to do it. If it's going to take away from Tuesday's flag football game, I'm not doing it. I don't know if I still have that energy.

Shaan Puri

Well, you can't turn that switch off, right? Because I saw you on Instagram, like, I don't know, a year ago or six months ago or something like that. You were like, "Pickles!" Yeah, you were like, "Guys, pickles!" It seemed like the guy who was saying "coconut water" when nobody was talking about coconut water. You were talking about pickles. So, me and Ben started paying attention. We were like, "Hey, what's Jesse doing? It's something with pickles." Well, okay, he's kind of right. Yeah, no, Brandon Pickle. So, describe this pickles opportunity that you see now. Currently, this is present day now, right? We're done with the past. Now we're talking present and future. What do you see in the pickle market?

Jesse Itzler

Well, like, 245,000,000 Americans eat pickles every year. It's like 75% of our population eats pickles. And again, it goes back to our running conversation. I'm starting to see pickles at races.

Sam Parr

at the

Jesse Itzler

At the aid stations, they never existed 10 years ago. Pickle juice never existed 10 years ago at the aid stations of marathons in your local 5th camp. And now they're... yeah, yeah. So that made my intent.

Sam Parr

Was that it? It has a lot of salt in it. When I grew up, all my Black friends would say that they would drink pickle juice in order to avoid a hangover.

Jesse Itzler

Oh yeah, in Russia, it's a big remedy for hangovers. But my... it put my antennas up like, "What is this?" You know, just like when I saw the first thing of coconut water on a shelf. I'm like, "What the hell is this? I just ran a 100!" So, I started thinking about it and I'm like, "You know what? I can't even name three pickle companies." I love pickles, and I don't even know.

Jesse Itzler

what they want

Shaan Puri

By the way, this is the part where he's going to bring in a focus group of 10 people. He's going to say, "Name a pickle company," and nobody could do it. Then he's going to be like, "That's the business plan."

Jesse Itzler

Well, listen. I researched the **seven best tasting pickles**, and of those, I think it was the Today Show that did it or something. You know, it's like someone credible did it. I only knew one of the companies. So, I'm like, if I only know one of these top seven best tasting pickles, there's a problem in the marketing of pickles. It's a marketing problem, and I'm a good marketer. That's where it started. I'm like, this is a category with no innovation, no fun. You know, **75% of Americans eat pickles**. The average American eats like **10 pounds a year**. That's more than cereal! And I'm like, I like it here. I like this space.

Sam Parr

I I'm a I'm a pickle guy too jesse same is

Shaan Puri

it clausen like the big brand is that right

Sam Parr

I like Clausen. I like Mount Olive. Is it called Valsic or Vlasic? I like that company, but I think Mount Olive is the biggest one. I always get the little ones that look like a witch's toe.

Jesse Itzler

are you wearing a metal alchemist pickle shirt

Sam Parr

I'm not

Jesse Itzler

look are you wearing I'm not I'm not I'm not big

Sam Parr

I don't see no around

Jesse Itzler

With a Claverson kitten, I won't disrespect that company. Alright, I don't even know, but I'm just saying, have you ever seen anyone wearing a hat?

Shaan Puri

like oh

Jesse Itzler

my god it's like

Shaan Puri

I'm convinced. In fact, we're texting Mr. Beast right now. We're going to come into this market too. You just made a mistake, my friend. We're bringing our influencers into this market. I believe you on this opportunity.

Jesse Itzler

why do that let's just let's get the beast on the phone let's partner with the beast beast pickles

Shaan Puri

that's right that's right who needs matt david you got me and jimmy now

Jesse Itzler

mile

Sam Parr

yeah where's david

Jesse Itzler

I need to

Sam Parr

go get ben affleck he seems like a good pickle guy

Jesse Itzler

I need to know about beast as low aggravation though I only want a low aggravation partner

Shaan Puri

well I don't know about that one

Sam Parr

mount olive does 220,000,000 in revenue a year privately owned

Jesse Itzler

it sounds it sounds doable man sounds

Shaan Puri

like our money right guys yeah

Jesse Itzler

yeah I wanna thank them very much

Shaan Puri

holding it for us yeah

Jesse Itzler

for holding it

Sam Parr

yeah yeah shoot a text

Jesse Itzler

over to ceo of olive and just let him know to keep that money warm for

Jesse Itzler

us alright

Shaan Puri

He'll be there soon. What other ideas you got? Because I told you, I was saying, you know, you'll get this because you're a rap guy. When you go on certain shows like *The Breakfast Club* or *Sway in the Morning*, there's an expectation. Like, "Okay, if you come on here, you gotta freestyle." We're trying to do that in the business realm where it's like, "You come on here, you gotta bring fresh ideas." You can't just only talk about your history. And you told me, "I got 50 ideas in my top drawer." I said, "Alright, say no more," but you hinted at me.

Sam Parr

By the way, the pickle names sound like rap names: **Sweet Gherkin**, **Bread and Butter**, **Kosher Dill**. Like, these are all rap names, man! Yeah, yeah.

Shaan Puri

Yeah, we're about to have this hilarious pickles. Alright, tell me about this idea. You gave me three words; I don't know what the idea is, but you said "ready-made 8-ounce drinks." What do you have in mind?

Jesse Itzler

yeah so I mean I I've been accumulating ideas in my in my top draw for 35 years I love starting dance sean you know but yeah I mean I don't I don't mind by the way if you guys want to rum anyone wants to rum with this you can I'll take a 1 penny royalty I'll give it to charity no I think like I go back to 5 hour energy the brilliance of 5 hour energy is they took a you know 12 ounce energy drink they shrugged it down at 2 and a half ounces right that's what 5 hour energy was and why did it work they they only I believe I believe they only have predominantly sold stores that would put it on the countertop when they started out so like it wasn't buried at gnc on the bottom shelf and then it was like on the countertop at checkout impulse buy they were selling 10,000,002 and a half bottle ounce bottles every week 10,000,000 when I look at when you look around retail at the counter at checkout of retail the countertop is incredibly crowded at you go to whole foods there's gum there's mints there's this there's that there's chocolates everywhere you go gas stations there's lottery tickets and the only place that I found like where there's open area are liquor stores if you go into a liquor store you don't see the the the the the self state you know the stands and the crowded space and all the tchotchkes and stuff that you see at gas stations and at at grocery and and other retailers and I think there's a tremendous opportunity I was gonna call them quickies to have like ready made shots same thing as as 5 like of your woo woo lemon drop whatever your favorite kamikaze ready made drinks are right at the countertop that are already made fresh ingredients you know where people could just come and grab and go and have a ready made cocktail that they could bring to tailgates parties etcetera I'm not saying it's gonna it's gonna be great goose vodka but I see an opportunity and if not that someone should go make a deal in in in a very fragmented k now you got me thinking sean now I'm not this wasn't even on my radar but here we go it's like the freestyling that you were talking about I was pointing at that really even a better idea would be to go liquor stores are that is the most fragmented market out there they're all mom and pops there's no like chain of liquor I mean that like you know you go to your local liquor stores like the guy my neighbor owns a liquor store I go there like get the wine and this and that do a roll up go pay someone for go rent the countertops of all the liquor stores and then go to nabisco or one of the big boys and be like hey guess what I own 10,000 countertops

Jesse Itzler

You wanna put your widget there? You wanna put your *fucking* widget there? Keep the money watcher. Keep the money watcher. Oh.

Shaan Puri

I love it yeah the the

Jesse Itzler

Real estate... we could probably talk for 15 minutes about the opportunity and come up with 10 ideas around that. You know, that's where it starts. It starts with just like a bad idea or a better idea—the idea.

Shaan Puri

Yeah, yeah, yeah, exactly. You're kind of like... I think the background of rap—I'm not joking about this—I think the way the brain can sort of like...

Jesse Itzler

that's

Shaan Puri

Not censor itself and wait until it has a fully formed, perfect idea, but actually just start to go. Then know that, "Oh, I'm gonna hop from this to this to this to this." There, yeah, that'll be the line. That's all I need to do is get to that one line.

Jesse Itzler

I I'm gonna show you this too this is this is something I'm selling now

Sam Parr

this is

Jesse Itzler

I don't know if are we on are we

Sam Parr

just on this youtube too

Jesse Itzler

are we on yeah only here

Sam Parr

no video video video bro

Jesse Itzler

This is by 2024, all planned out. This is next year, fully almost fully dated. What my year looks like, my race is...

Shaan Puri

my what's orange there's a lot of orange on that what does orange stand for

Jesse Itzler

Orange, orange! So, when Sarah sold Spank, she wanted to do a lot of traveling. This year, we committed as a family to go on the road. So, all the orange, as crazy as this looks, is all travel. Wow! We're going to Africa, we're going to New Zealand, but it's all mapped out.

Shaan Puri

yellow what's what's yellow and what's what's green or or blue whatever that is

Jesse Itzler

Yellow represents my races and events. Green is for my speaking engagements, and green also indicates birthdays and other events.

Shaan Puri

This thing's dope! Now, I wanted to ask you about this because you are super legit as far as what you've actually been able to accomplish. Your level of success is impressive. You do stuff like this; you have the "Big Ass Calendar Club" or whatever it's called. That's a product you make—it's like a course you have. I'm always surprised that you're doing those things. So, what's your thought process on picking projects? Or the running club—how do you choose which projects to pursue?

Jesse Itzler

Yeah, I mean, I think this goes back to the earlier question you asked me about reinvesting in other businesses and stuff like that. How old are you guys? How old are you, Sam?

Sam Parr

34

Shaan Puri

I'm 35

Jesse Itzler

so I got I got 2 decades on you guys and but I got I got the most experiential decades I believe on you guys your the forties fifties thirties forties fifties you know for me there's I'm in I'm in a coaching space you know I speak a lot I have coaching programs the calendar but even the events that I do the run running races and this kind of stuff it it all has an element of getting people to do more than they thought to inspire people to do more than they thought they could but but to answer your question and the reason why I just said that is the gal who works with us in our family office was looking at all the businesses and and asking me like I don't have a sales rep on my payroll I don't I'm not going crazy on the marketing and this and that and it's really word-of-mouth and she looked at the numbers and she's like you know do you want to scale this and what are you doing why don't why don't you just go do the liquors idea or the airplane idea or this idea or that idea or any of the ideas in your draw and I pulled out my phone and I said kendall all these are from today all of these messages are for today pick 1 read it I said I can't and it was like you changed my life or this has really inspired me or you you know I did this or I saw my parents I haven't seen my parents in a long time and you know I talk about the importance of that very often you know about not losing sight of what you already have while you're chasing your entrepreneurial dream your health your family your friends there's no business in the world that would give me the return on investment that I'm getting right now there's nothing I could do what build another marquee jet work 20 hour days I mean like that's not gonna give me that sense of impact legacy for my kids and just the feeling quite honestly that I have I mean like it's indescribable a wire is a wire you get the wire and it's like the same feeling you get when when you sell a business is the same feeling you get when you finish the mar a marathon you walk an old lady across the street or you do anything that makes you feel good about yourself I swear to god and I have the right to say that because I sold 5 of them I have the right to say that it's the same feeling and for the for for very very for a lot of people chasing that waiting 20 years to sell a business or something to have that feeling when I feel like I get that every single day and that's a really powerful place to be in your life at 55 and and that's the reason man and and so you're right I have these businesses and you know there's no real plan around them people like what you would I don't I don't know I'm just enjoying how it's making me feel right now and what's wrong with that I gotta scale just to scale because everyone told me I had to scale I don't wanna do that man right I did that

Sam Parr

So, a question that we like to ask people is a really simple one, but we learn a lot from it: **What do you do with your money?** You have a really interesting lifestyle. I agree with you; I don't like the Elon Musk path of making all these sacrifices and doing things solely for the sake of humanity. I'd rather have a fun life, and you have a really exciting life. I’m a former college athlete and runner, so I enjoy watching what you're doing. I like to work out, do these podcasts, and have a lot more fun than just working. So, what do you do with your money? When you're financing this, are you just using your speaking fees to fund it? Do you have your Marquee Jet money in just one big account in the markets? How's your portfolio set up, and what are you doing with your money?

Jesse Itzler

Well, just, you know, it's... I don't know, man. Like, we never really think about it that much. I know that's... I don't want to belittle it or sound in any way obnoxious. In fact, I'm incredibly grateful. But like, it goes back to the relationship with money from the beginning of the conversation. We're not trying to triple it or quadruple our money. We don't really think about it. It's like it's spread out strategically, and we live our life.

Sam Parr

What's your monthly burn? I mean, what does one need to spend per month to do that?

Jesse Itzler

I like to ride my bike. I like to run. I like to swim. I like to speak in public. I like to be around my family and friends. Whatever that costs me, Sam, is what I'm going to spend on it. How's that for him, sir?

Sam Parr

yes sam not so much sam

Shaan Puri

I want to ask you about something that you have talked about, which I really liked. It's around your life philosophy. You have a few of these that have made an impact on me. I don't know where I saw it—maybe a TikTok clip or something—but you were talking about this **3-minute daily thing**. You said, "I can network in 3 minutes." I forgot exactly how you phrased it, but it was like, "I can invest in my friends, my network, in just 3 minutes a day." I'm always interested in anything that's like, you know, the **6-minute abs**. I tend to be interested in shorter time frame type things. Do you go with compliments? What were the other ones? You go with compliments?

Jesse Itzler

complimenting congratulating consulting

Shaan Puri

Explain that philosophy because I've been doing that now. I basically go through my text list and I'm like, "Who's somebody I could compliment?" Boom! Send it out. They love it because they're like, "You know, I'm thinking of them. We haven't talked in a little while." It's really simple for me to do. This is kind of like a very effective little tip I want you to share here.

Jesse Itzler

well in my twenties I didn't have a way to to I had no I was really on a super tight budget I was writing 10 handwritten letters I'm in a year not every single day but pretty much writing about 10 handwritten letters a day and that was my entire marketing strategy and I realized that you know it's a great way to get through the clutter of email dms social you know all this stuff because because a lot of people don't check their emails or their assistant does or whatever but everyone reads a handwritten letter so I the 3 minutes a day is you know I have sent a text you mentioned the kay academy coach kay I sent a fluent to carolina not too long ago and I sent coach a a text thanking him for having the event and I said you don't need to respond I just wanna let you know like it makes me feel like an 8 year old for 5 days a year I wanna thank you for for doing this I know you don't have to do it and it took and like I realized like he might share that with his team like we're having an impact like look at look at this note or tell his wife he might do nothing but now if I see coach k I have permission to go over to him and say coach I sent you a text like I know if you got it but like I have that permission to do it I'm not coming out of left field like oh hey coach you know like woah you just so that took me 45 seconds to hit send write it and hit sent so I was like okay if I did 3 of those a day and just took 3 minutes and just started hitting friends suppliers manufacturers inflow whatever over the course of a year I'll send a 1,000 I will plant a 1,000 permission slips all over the country and world 3 minutes a day so in carpool line when I take my kids to school or pick them up I just fire off a couple of emails or call them or whatever so that was that theory the compliment congratulated consoling is really just kind of three things that I I like to to remind myself to do to maintain and build authentic relationships authentic relationships not relationships authentic relationships so for example if you have somebody in your life that's grieving and you don't reach out to them and you guys are young but you'll see in the next 10 years friends will start to get diagnosed with stuff parents grandparents are gonna pass away like your life's gonna change man if you have someone that's grieving and you don't reach out to them they will never forget it they'll never oh the the the you can't human nature you can't even help but take inventory who reached out and who didn't you're just aware I just lost my father I know everybody that called me I know everybody that didn't call me and the people that didn't call me don't get a pass they don't get a pass so you always wanna consult the people that you you know something happens to a friend in your life that's great you wanna congratulate them you know and then you wanna compliment you know sean man sam listen you guys have an amazing podcast you did it yourself you know you guys decided to like sold some businesses and here you are you know bringing on inspiring people to inspire entrepreneurs all over the world and I just wanna congratulate you on your success man I'm not you know I you just call someone out of nowhere

Sam Parr

you default to calls or texts

Jesse Itzler

Either way, I just think I personally like handwritten letters. Here's why: I feel like the intent it takes to actually get a stamp, lick it, go to the mailbox, and put it in the mailbox is completely different than just sending a message electronically. So, probably like in the pecking order, you don't have the ability to do that because it takes too long. But at the end of the year, I do like to write 25 to 50 handwritten thank-you letters every year. I have a whole year-end process that I kind of teach people, and that's one of them. You know, you compliment, you graduate, and you get soul. You do that for people. For example, if I hit you up—God forbid you had something bad happen—and I don't even know you, I just met you for the first time, other than the question about my burr rate. I love you, so if I were to call you up after one meeting and say, "Sam, man, I heard about XYZ. I'm so sorry that happened to you," and then four months later, I call you up and say, "Sam, man, you guys just hit 5,000,000 downloads a day! Congratulations, man!" Then I call you up again at the end of the year and say, "Sam, I just want to let you know, man, about that question you asked me about my burr rate. I rethought it, and I want to compliment you because you asked the tough questions. You know what? That's the seat you're in, and I give you credit for asking questions like that to people on the other end. I really admire you for that." If I do those three things in that year, you're going to think differently about it.

Shaan Puri

Oh, you'll be his hero. You'll be all of our heroes, to be honest with you. That'd be...

Jesse Itzler

incredible alright well well dad

Sam Parr

come on come on come on

Jesse Itzler

Sean, you laugh about that. We're laughing about it, but let me ask you a question: who doesn't want to be a hero?

Shaan Puri

you're right

Jesse Itzler

Who doesn't want to be a hero? If you're telling me I don't have to run into a building and save someone, I can just do that and I could be a "quote unquote" hero. You know what? I built my career doing that.

Shaan Puri

Well, this is about relationships. You also have others about skill building and life experiences. Explain some of your other kind of life rules because I think these are really worth sharing. You know, people will be entertained and inspired by the business stories, but my hope is that this actually was just buying the right to drop a little wisdom on them at the end here. Because this is the stuff I've liked the most from you and your story. So, talk about, you know, the sort of *misogi* or the *Kevin's rule*. These are pretty foundational.

Jesse Itzler

yeah well that goes into kind of the planning that I showed you on the calendar and I really do do 2 or 3 things every year at the beginning of the year this is actually perfect timing I don't know when this is gonna air but like november december when you look into 2024 or the next year I try to have one big year defining thing on my calendar every year last year was my bike ride across america 2015 it was living with the cl the book I wrote 2017 I lived on a monastery 2016 or something I started 29 or 29 this company with my partner so there's an old japanese ritual called the misogi and we took the liberty to kind of create our own version of what that means but basically it means that every year you do 1 or the way I've interpreted it is you do one big year defining thing and you should have something to show for it every year by the way if you're 35 years old I don't want I'm just rounding up here and you live to be 85 so you have that would be 50 year defining things between now and the end of your and the end of your run that you have on your life resume that's pretty damn incredible the second thing I do is something I call kevin's rule named after my friend kevin which is every other weekend I do something I normally wouldn't have done like instead of watching like a georgia the georgia football game I might take my kids fishing I might go to a conference I might you know watch spend a couple of hours learning something I I didn't know I coined it kevin's rule because kevin and I were camping in mount washington with our kids and it was like I'd go kev there's 8 it's like the winter it's snowing we're sleeping outside in a - 40 sleeping bag - 20 sleeping bag I'm like kat there's 8,000,000,000 people in the world man it's only us on this mountain you know it how often do you do this because he invited me he's like oh every other week he's a police officer I do so every other month I do something I normally wouldn't have done I'm like what do you mean he's like so at the end of the year I got 6 mini adventures if you're 35 and you live to be 55 and you have 6 mini adventures that's 300 mini adventures and 30 50 I'm sorry 50 year defining things you're misogi and 300 mini adventures sean I don't care how much money you have or how little money you have at the end of your run if I go to you and you're 85 years old on your deathbed and you're like jesse mann thank you I took your advice listening to my podcast and I now have 50 unbelievable adventures I've done the grand canyon I've taken my family and I have 300 mini adventures that I've done and by the way it only took 6 days of the 365 days of the year 7 days of the 365 days of the year it's a 2% is that 2% 6% what is that

Sam Parr

we have a rule here

Shaan Puri

we don't do public math so don't worry you're off the hook

Jesse Itzler

I mean, I never got it. That's a great run. That's a great run.

Sam Parr

Have you ever hung out with Rob Dyrdek? You guys are really similar. We had him on, and I think I've said publicly he's one of my favorite people. You have a similar quality where you just have a framework, and you know what you like. You stick to it, and you're really intentional. I appreciate that.

Shaan Puri

On your terms, which is what? Well, I think the highest calling thing we respect on the pod is somebody who defines their own terms and then lives by them. Even if you don't... even if somebody doesn't.

Sam Parr

Successful people don't do that. Even people who are wealthy often say, "I fucking hate my life because I'm tied to this job that I actually don't like doing." You're a great example. Your definition tends to be exciting and awesome because you're doing all these adventures. But it didn't matter what your framework is; you've done a cool job of defining it and sticking with it. I appreciate that.

Shaan Puri

Well, one cool thing that's different is Rob's approach, which is all about maximizing efficiency. He's focused on how much time he has, how to allocate it, and how to get the most done in that time. Whereas I feel like Jesse has almost a different relationship with time. It's about how to have the maximum number of incredible experiences, amazing relationships, and moments. Whether that moment took 5 seconds, 5 days, or 5 weeks, it doesn't really matter. It's like maximizing—kind of like squeezing the juice out of the fruit, you know? Versus trying to optimize every moment.

Jesse Itzler

In a generation of hustle and grind, which is so obvious—no shit, you gotta work hard—that message gets lost. You don't want to give up your twenties, thirties, and forties, and certainly not your fifties, if you can avoid it, just grinding and chasing something that you can get the same feeling doing something else.

Shaan Puri

Well, we feel lucky for having you on very early in the podcast. Sam introduced me to a guy, Mike Brown, and he said one line on the pod that changed my life. He goes, "Yeah, my theory of life is find the people that you love and then do life with them." I just thought, "Oh, if there's a north star for me, like that's the new north star." You know, maybe something more wise will come take its place, but that's it.

Sam Parr

and that's the pie