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

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. You want to put your widget there? You want to put your fucking widget there? Keep the money warm.

Yeah, keep the money warm.

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

Um, all right. Well, welcome. We got Jesse Itzler here, um, also known as— I think he might be the richest runner white rapper in the country. So congratulations, my friend. We, we, we are excited to have you here.

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

So right on. So, you know, I'm excited to talk to you because you've done a bunch of amazing things. We've talked about you on the pod and we sort of spoke it into existence. I think we talked about it. Somebody might have sent you a clip. I'm not sure. But you, you reached out and said, hey, I'd love to come on. You have— I'm just going to read a couple of these things, so I'm going to flatter you real quick just so that the audience understands kind of just your background. So like we said, started out trying to make it as a rapper and ended up creating a jingles company. So you were making jingles for, for sports teams. Ended up selling that, then created Marquee Jets, a fractional jet owning company. Sold that to Berkshire Hathaway, which Warren Buffett obviously runs and owns. You're married to Sara Blakely, founder of Spanx. You are an epic sort of fitness athlete yourself. So prolific runner. I read your book. The day I got really into you is 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. And yeah, you've created a bunch of companies outside of that, partnered with Zico Coconut Water and doing a bunch of prolific things. So you have a very prolific career, but the start was like anybody, it was humble beginnings. So talk about the early days when you were trying to do the— let's start with the jingle company. You, um, you told me you were, you were sleeping on couches at the time trying to make it and, uh, describe kind of what was going on at that time in your life. What was the plan and what were you going through and how did you come out of that?

Well, I grew up in New York in the '80s when rap and hip hop was starting to emerge in a bigger way. And that, it, that was the intersection of, of that happening and me going to college. So I was really into music early on. And while all of my friends in college were writing resumes and going on job interviews, I was like, I'm making a rap record. Like, I, I'm, why would I waste my time making a resume? I wanna make an album. So it was like kind of, that's 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 and I didn't have much, like I wasn't super connected. I didn't have like a lawyer. I, no, I did it all. I shopped it myself, but I ended up getting dropped from the label shortly after. And I got into writing jingles or for companies and theme songs for sports teams. And that was kind of my first entree into, you know, I pivoted. It didn't work out for me in the music business, but I still loved music. So I stayed in there and I started doing jingles and Yeah, that's how I kind of started out early on.

You told me you were sleeping on couches, um, trying to make it, and 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?

Right. So I was, I was writing theme songs for sports teams. I was 22, 23 years old. And my business model was to write a song on spec and then cold call a professional sports team, try to get a meeting with them, try to like, you know, get in there. And then if I was able to get that meeting, convince them that they needed a theme song. And that was my business model. And at the time I was, I was, I was bouncing around from couch to couch. I wasn't homeless, but my friends were. I just moved to New York from Los Angeles and my friends were putting me up as I tried to figure out how to do it. I had no money to go in the studio to write any more songs on spec, so I needed money to fund that production. So a music manager said, you know, I, I, hey, I believe in you. I'll give you 10 grand for 10%, but I want to own you for the rest of your life. Basically 10% of anything you make. And I was like, I'll take it because I needed the money to go in the studio. I thought it was a deal of the century. You're gonna give me 10 grand. And all I'm gonna do is pay you if I make it. Like, 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 and said, if you're in an emerg— she asked me where I lived and I said, as of Monday, I have nowhere to live. I was getting kicked outta my friend's house on Monday. She said, if it's an emergency, you can come live with my roommate and I. Monday, my friend kicked me out 'cause his parents were coming for a week and I'm like, this is an emergency. So I was living at Melissa's house and I told her about this opportunity and she said, well, why don't you go talk to my father before you give away 10% of your future earnings? And as it turned out, her father was a very successful entrepreneur. He owned a company called Kenny Parking, parking garages in New York, and was, um, I think the second largest shareholder of the New York Yankees.

You're like, Melissa, your apartment is really nice.

What was amazing about that was it really wasn't. And that's why I really was taken aback by I knew her dad was an entrepreneur. I didn't know the extent. And, um, she, you know, she sent me on, by the way, his name is Lou Katz. He passed away a couple years ago. He was an incredibly influential guy in my life, and this was my first encounter with him. So I went to, not to belabor this, but I went to see him and it's, it's really relevant for anyone listening what he said to me as a 22-year-old. He, I told him my dilemma. I'm gonna take 10 grand for 10% of my life. And he said to me, he's exactly what he said to me. He said, Jesse, you know, will you make this business work without the 10 grand? I said, Lou, I'm onto something. I know I can make it work. There's a, I know I can. And he, he took his notebook and he literally threw it on the ground and he said, I didn't ask you that. I didn't ask you, can you? 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, I said, will you, son? And I said, yeah, will, Lou, I will. He said, well, tell him to take the $10,000 and shove it up his ass. Go make it work. And I did, you know, like it was a really powerful lesson and like, you know what? I signed up for this journey as an entrepreneur. Let me go figure it out. Let me go. That's what I want to do. Let me go figure this out. And he keep breathe. He blew 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, the whole will versus can notion, you know?

And why, why is that so powerful? The will versus can?

Well, because it's, it really puts the pressure, you know, Billie Jean King in a book, Pressure's a Privilege. And it is like, we play for pressure. Sean, like as entrepreneurs, that's what we want, man. And you know, I recently did a race called Ultraman. It's a 6.2-mile open water swim, a 265-mile bike, and a 52.4-mile run. And I thought to myself before the race, that exact thing, like, I think I can do it, but I'm never gonna know unless I sign up for the race, put myself in a position where something incredible can happen or not. But I gotta put myself in that situation. And now it, it's up to me, like, will I get it done? You know, will, what am I willing to do? Am I willing to suffer for that one day for, to have the next 3 decades have that in my memory bank and have it on my resume? And, and I, and I am will, and I am willing to do that. And, and I did.

So, you know what's really funny? Uh, after you told me that, so I did a call with you the other day to just prep for the, for the pod, say, hey, you know, We're going to talk about, I'm thinking about talking about this, this and this. You have any good stories? And you told me this, this will versus can thing. And the next day my wife was literally like, she's like, hey, can you take out the trash? And I was like, no, no, no, baby. It's not about can I take out the trash. I will take out the trash. And she has no idea what I'm doing. And I've been doing it all weekend. I've been, because once you see it, it's actually everywhere. Ben texted, Ben who's listening on this thing right now. He texted me this morning. He's like, He's like, hey, how'd you eat this weekend? We're both like on a fitness kick. He's like, can you stay locked in from now till Thanksgiving? And I just, I was like, oh Ben, you asking me can? 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.

Well, think about how many times in your life someone said, you, you say something that you've done, like, you know, I did, you know, rim to rim. I'll take physical activities or I climbed Kilimanjaro and You explain to someone, they're like, oh, I can, I can do that. And I, you're like, in the back of your head you're like, yeah, you probably can, but you know, will you do it? You know, there's this like, it's a huge difference between like, oh, just checking the box because you said to yourself, I can, versus actually going through and doing it.

By the way, Jesse, I have one other story that you, 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?

I've been there for, uh, 18 straight years.

Okay, okay, perfect.

That's hilarious.

So you went to this thing. So for those who don't know, Coach K, he was the, the greatest college basketball coach at Duke. I went to Duke, and, um, my roommate Trevor used to volunteer at Coach K's fantasy camp. And volunteer was literally volunteering. I was like, so what are you— you're staying over from break? Because it's like 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 you getting paid? He's like, I don't think we really get paid, but, uh, you know whatever, like you just said, put himself in a position for something good to happen. And so, and what I did, what he didn't know and what I didn't know was the only people who go to this camp that costs like $10 grand to go to are basically like business ballers trying to like live out their dream of like, oh, as if I was an athlete. And he's, he, so he would, all he was doing was driving the shuttle back and forth between where y'all were staying and the thing. And he's like, dude, it's amazing. He's like, just hearing these conversations, what they're talking about in this like 9-minute shuttle ride. He's like, every night he would debrief with me ideas that he heard. He's like, oh, this guy said that he does this, this thing over here. This guy said he does this. And he told me, he goes, I met this guy, super charismatic, like this guy. He loved this guy's energy. He goes, and he tipped me $100 for this like 10-minute shuttle ride. And he, late, I told him, he, I told, uh, I was mentioning to him that you're coming on the pod. 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, uh, we had a business idea at the time and we needed to convince this, uh, famous chef in LA to come fly out and partner with us. We had no money. And so you, you plus a little like side job that I had became the money we paid for, for the ticket to fly that guy out, which definitely changed the trajectory of our life. So little did you know.

I, I love that. And, um, yeah, I've been going there for, since I'm 35, it's for guys 35 and older. And it's not to chase some, some crazy dream. It's a combination of, you know, meeting amazing people and also kind of like, there's not a lot of times— 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, 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. And it's really one of the few times in my life that I get that chance and I love it.

I don't know, man. I follow you on Instagram. It seems like you live like an 8-year-old a lot of times. I'm pretty sure I just—

I do, I do, I do, I do.

I shouldn't say that. I'm pretty, I'm pretty sure I just saw you like in an RV with like 8 friends just like running around the country.

Right, exactly.

It seems like you, yeah, it seems like you got the 8-year-old life kind of nailed down.

I like to give myself that excuse, Sam. I guess you, but you're right. It's more than once a, more than 5 days a year.

Yeah, I, I think, I think you've done that all right. You, uh, and then was your first, um, kind of major business Marky Jet? So you went from, did you go from jingles to jets?

Yeah. So interestingly, I had, so 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, um, I was doing jingles for like, I, I honestly like Turbo Bubblegum, this like bubblegum company that no one ever heard of. Like just anything that would be—

Hey, our podcast intro needs a little sprucing up if you wanna, if you wanna dust it off. Yeah.

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 Paint 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, 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'd 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've paid the Knicks 10 grand 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. So I would take the songs they play in the arena, add my original song with great moments in the team history and sell 'em 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 million, 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.

What was your take home after that?

I had a partner and at the end of the day, I think the, on the first $4 million, I made like a million and a half or, but by the way, a million and a half dollars to me, all the money. 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 go to the, wake up at the 8 and go to the ATM. I would get my, a printout of my balance, 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 back to bed. I'm going back to bed. Shit, I'm making more money in bed. My partner convinced me to take all $1.3 million that we both cleared after taxes or whatever it was, and reinvest it to, to, to get like exclusive deals in all the, like we made the business, we reinvested it in the business and actually made the business a lot bigger and we got our earnout. And then, 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 the plumbing supply house. My mom raised 4 kids. The, the thing, the, I had no relationship with money. That might sound weird, but like people talk about relationships with, 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, how to act around it. I was very immature around new money. And you know what happened to me then? I lost it because I didn't know anything about it. And fortunately, I, I was able to bounce back through having other successful businesses and failures, but No one ever told me about it.

How'd you lose it? Just overspending, or what'd you do?

Overspending, thinking like, oh, that was pretty easy, man. I could just— I could do that again, you know. Um, what did you buy? It wasn't like so much what I bought. It was just, you know, helping my parents, spreading it out. I wasn't abusive with it, like, but just I didn't know how to really handle that.

That's pretty common, right? Like You know, Sean and I have a bunch of friends that, you know, we're both about 34, 35, and we have a bunch of friends and ourselves as well who had exits at a young age. And the thing about selling a company, it's different than— there's usually two types of people I've noticed is people who have cash flow businesses, or they're like a lawyer or something like that, or they own a law firm, something where your like income is going up a nice amount every year and you get used to having that cash flow. And then the other group of people are typically young folks who sell their company. And typically those people are like me, where I paid myself $20,000 year 1, $20,000 year 2, year 3 was $50,000, year 4 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. And that's like a pretty, that's like a pretty common thing is I don't think, I don't know if most people blow it, but I think it takes about 2 or 3 years to accumulate and kind of get used to and learn what to do. But there's no one to teach you.

The problem is I'd always been taught, oh, if you're a, like a millionaire, was, that ain't shit. Was the, no, but I've been, no, I've been taught the opposite. Like if I saw a millionaire, that was like the pinnacle. Like he's a millionaire, right?

Man.

So I always thought like, oh, I have a million dollars. That's all I need to have for the rest of my life. I'm a millionaire at 27. And that's, that was the relationship that was wrong.

Right. Yeah. You could spend that, you could spend that easy.

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

You— I'm a big believer that most of life, most of your life kind of is a result of this, 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 and you still have— you're only 27, you still got all your life ahead of you. Do you at all remember like the conversation you had with yourself? Like, all right, Jesse, so like now X and whether X was a good, good a good conversation with yourself or misleading one? Do you remember what the conversation you had with yourself at that point in time was?

You know, it was interesting 'cause Sean, 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 a lot of money around, 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 yourself. You can go down a and spiral downward very quickly. And you know what I was making, what it took me years to make and build and sell, and my journey to get to that point 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, I cleaned meat trucks that didn't work. I sold chicken, shrimp, and meat door to door. That didn't work. I mean, jingle company, they, I, it went on and on. So, you know, I had really worked so hard and, and at the same time, like I had 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 wanted, 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, with Laird Hamilton, and you were saying how that, he was saying how that, you know, you, one of you guys was saying you need that anger to inspire you. Like you need 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'm, I never wanna lose that underdog mentality. I never wanna be like, I'm at the top of the mountain. I, 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 salesmen 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 Starker's making so much more than me. We're in the same basketball run. Like I gotta catch Starker, you know?

The, the Marquee Jet thing. That's interesting though, 'cause that's like, totally outta left field. So, and that seemed like a, a, a way bigger win than the jingle business.

Same partner, right? Same, same co-founder.

Yeah, same partner. It was a much bigger win and it was 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, you 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 '90s when we started Marquee Jet. You can buy your own airplane if you had $50 million, 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 the little white space there and said, you know, we only wanna 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, um, have a plane available on short notice. And that was the idea around selling a 25-hour check card that were both like, worked like a debit card. So if, if you and, if you and Sam Sean 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 Coconut Water, they ended up buying us. So, but anyway, that was, that's what happened. We were guests 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, um, figuring out like, man, we need a lot of airplanes. Where do we go for airplanes? And, uh, and then started that journey of, of building this company.

So you walk in, you walk into NetJets and you're like, hey, um, I'm Jesse, former rapper, jinglepreneur, 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?

Well, at first we didn't, they kicked us outta 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 multi-billion dollar company let two kids that didn't break 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, 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, Sam, I'll do this for you, Sean, but like, can you do this from, like, I don't know how, that's not the MO. 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 Chris, um, a famous singer was performing in his hometown. His daughter wanted to bring her sweet 16 to the event. The guy says, I know, you know, the manager, can you help, help this guy get some tickets and do anything special? Turns out I get the, the guy's daughter as a backup singer for one song with the mic off. Everyone in 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 NetJets a year later. I need 650 airplanes. I call him up, I'm like, Jim, you're never gonna believe this. The, the guy who got your daughter on, I have an idea for a thing. He gets me the meeting. We get thrown out of the meeting 12 minutes in because they're like, we're not giving two 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 to me? He goes, Rich Santulli, my partner, he doesn't give anyone 12 minutes. He goes, this is something. 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 could never sell them in a PowerPoint, which was like what everyone— guy sees 100 PowerPoints every year. We brought in our own focus group. We had 8 people in the lobby.

Mm-hmm.

And they walked in one by one 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 jet card. 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, a couple years later, we had more customers than NetJets.

That's crazy.

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. And it turns out that 8 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.

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, was right behind me on the wall. You know, when these guys—

at that meeting.

Yeah. We brought, we brought 'em in, we brought 'em in. And when we said, when, when, when we, they got up one by one and explained why this card would work. And you know, I think what they realized was they had been pitching to a, a much older corporate client. And that they, what they realized, I think in the meeting was here are these two 27-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 two 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 and, you know, like year one, we did a, I think we did like close to $200 million in sales year one. And I remember going into his office and, and asking, I said, Rich Santulli, who is like, he knighted me, man. He knighted 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 me 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, et cetera, 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, Kenny and I, my partner and I, that he wanted to bet on. And you know, I just wanna say this for, 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 in our own focus group to start a company that does $5 billion 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, um, 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, and it worked. And then we had an amazing, amazingly fruitful relationship and partnership with NetJets until we exited. Our software is the worst. Have you heard of HubSpot?

See, most CRMs are a hobbled-together mess, but HubSpot is easy to adopt and actually looks gorgeous.

I think I love our new CRM. Our software is the best. HubSpot, grow better.

All right 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 I have a lot of peers and friends who are CEOs of companies, and I'm able to ask them all types of different questions. And it all started because I used to run this event called HustleCon, and I would like convince these speakers of big startups, you know, you've probably heard of most of these companies, the founder of Grammarly, WeWork, Away Travel, Casper, all these cool companies. And I would sit in the green room with them and I would hear all these amazing stories, but I would also be able to learn like how to fire someone effectively, how to, how to handle things when the business isn't going well, how to handle things when it's going great. Like all these stuff that happens behind closed doors and it changed my life. And so I started this company, it's called Hampton. Joinhampton.com is the URL. Where we make it really easy to have a peer group and have a network of other entrepreneurs that are like you, similar industries, similar size companies. And so if you do 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, $400 million in revenue and they're publicly traded. Others are a little bit smaller in the $1, $2, $3, $4 range. But my partner and I, Joe, we review every single interview and we hand curate and hand select all these interesting people. So it's been a really wonderful community. So if you wanna be a little less lonely, if you want to 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, uh, enjoy the rest of the episode. Are you, um, so like, I, I, I, I think that all three of us might be a, a, a bit similar in, in business relationships where we're like, we bring the passion and some of the creativity and the Zero to One stuff. Were you good at running that company or were you, or did you have a good partner who was running it and you were great at kind of bringing some of the deals to fruition?

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. And then, which allowed me to focus on sales, which I was, which I was better at buzz, which I was really good before the in— before Instagram. I'm not so good at the now with Instagram, but back when there was no Instagram, I was good at creating PR opportunities and, and talk-worthy events. And for my era, that was really important. So no, I have never, I've never been the CEO of a business. I've never ran or operated a business. But I've been a founder I think 5 times.

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

No. So we, the original deal with NetJets was 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 it. So we had no risk. They were carrying all the paper. So if I bought, if you and if Sam, Sean, you guys bought 100 hours, we'd go buy 100 hours and it was marked up. So 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, you know, we have 4,000 members. We're doing $1 billion 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.

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

I don't even remember what NetJets sold to Berkshire for. I'm sure it's public.

This was before Berkshire owned it, is that right?

NetJets sold it to Berkshire prior to us. Okay. And then, and then we went to, now we're part of NetJets. Now G-Jets, now part of NetJets. Did you get Berkshire stock?

Because that would've been a good stock to just get in the deal.

I know, right? No, we didn't.

NetJets sold for $725 million in '98. And half of it was paid in stock. So that was, if that was a good deal for NetJets. Depending on if they— I don't know what the revenue was, but that's a lot of money.

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

$200.

I don't know what that means. What is $200 million there? That's not— that can't be membership dues. That's— that would be insane.

No, it is. Yeah. No, because our average, our average customer spent close to, I think it was $250,000 or $235,000 a year.

Gotcha. Okay. But it is more like GMV. So because you have to So your take is some spread between that and then whatever net— okay, gotcha.

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

Well, this is 30 years ago, so how about, 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. And, and by the way, the best ROI in that deal is I met my wife there. She was a customer of ours. and that's how I met my wife.

Um, you, you said, you, you told me something which was about getting the first customers. So before your wife was even a customer, uh, you know, you're like, I'm on this plane. I'm like, 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. You come up with the idea.

Cool.

Now how do you go get those first people to give you $200,000 to be a part of this?

Right?

That's like a, a huge, like, where did you go find those customers and, and tell the story of kind of how you got it off the ground?

Well, we were start— we started out, you know, I think the first thing that any entrepreneur, most entrepreneurs, at least in our position and at Marquis Jet, is we had to establish credibility. 'Cause if I was gonna sell you time on a plane and you said, who flies with, who flies with you guys? That would be my first question, or one of them. And I said, oh, my dad and my next door neighbor, you probably would leave. But if I was like, you know, Oprah, Bill Clinton, you'd be like, wow, they must have vetted this, you know? 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. And I heard about this, you know, they could afford time on a jet. I heard about a conference in Monterey, California that was just getting some traction called TED.

Yeah.

So I flew out to Monterey and, you know, I told the guys like, hey, I'm gonna go get my first sale. I'm going to the TED. I think called a TED Talk. They were like, what? You know, TED, and it's in Monterey, California. You gotta like, you can't even get there. You have to like, I connected through Chicago into whatever, rented a car, 5 hours to Monterey. I get to the TED, it's like Fort Knox, man. Everybody has a credential like this, like huge. And I'm like, you need a credential to get in here? There's no credentials to be found. So I'm thinking like, how am I gonna sneak in, buy someone's pass, like go into the room where all the qualified leads are. I'm in this coffee shop plotting, like, you know, my, my, my entrance or how I'm gonna do it. And every 2 hours, a wave of people come in and they're buying, they have these credentials and I'm like, oh, this is where they come on their break. And they're all buying lattes and muffins and these lattes and muffins and whatever. Lattes and muffins. So the next morning I got up at 5 and I bought all the muffins from this. I controlled all the muffin inventory. In Monterey, California. And I literally just waited. And this is a true story, by the way, and it's, it's been verified. You can walk. So 2 hours later, this guy, uh, the first wave of people on the break walk in and the guy orders a latte and a muffin. I stop him. Uh, they tell him that, that they could give him a latte, but they're all outta muffins. It's like fucking 9 in the morning. He's like, you're outta muffins? The guy starts walking. I stop him. I'm like, sorry, I overheard you. I actually have an extra muffin if you want a muffin. And he's like, you got an extra muffin? I'm thinking like, I got every single fucking muffin under the table, man. What do you need? And I started talking to him and he is like, you know, what are you here? I'm here for the conference. I'm like, me too. What do you do? I tell him what I do. He said, you gotta be kidding me. I'm in the market for a private jet card. And his name was Josh Kopelman. He owned a company called Half.com.

Famous VC, right?

Oh, he's amazing.

Now he is.

I bumped into him like 3 years ago at a retreat and we were talking about this. And anyway, he was my first sale. He was my first sale. And 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? And, and, um, he was my first sale though, Sean, to answer your question. And, and you know what happened after that? I'm gonna 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 every, um, DM and all that. Of course I did what everyone here would do. But he went to Mexico. He didn't expect the list of pediatricians that I vetted in case his kids got sick.

Mm-hmm.

He didn't expect me to make reservations every Wednesday at, at every night at 8 o'clock during spring break in Mexico in case he and his wife wanted to go to dinner. And, and, and after a couple of months of doing that, what he didn't expect me to do, he gave me the magic word. He gave me a referral. And that was rinse and repeat for, for 5 years. Until we grew this. So no, I was never the CEO. I was never the, the operator. I was never the COO. I was, I wasn't even, I don't even think I was on the org chart.

So I'm, I'm, I'm looking at your, check this out. Well, you're on the website. I'm looking at, I use Web Archive. I'm looking at the, uh, the 2005 version of marqueejet.com and I'm looking at your about page. And what's interesting, it looks like your senior executive team was not only awesome, it was like Amazing. 'Cause Ken Austin, I see, was your executive VP. Is that the same Ken Austin that went and started, is it Avión, the tequila company, and most recently started Proper Twelve with Conor McGregor? Is, is that the same Ken Austin?

And the tequila company with The Rock? Yes.

You've done a good job of hiring.

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

Well, it's also a sick product. I mean, you said you met your wife there. It's like, That's like the greatest line ever. Like, oh, do you— you're here at this jet company. So I know like you're of someone. I know you're someone interesting.

Definitely.

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

It was. 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. And I think we were the only one that made money. I might be wrong about that, but it was something that some—

including, uh, Garrett Camp, the guy from Uber, he created, he tried to do an Uber for jets, uh, that didn't work out. Right.

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

The other business you did a partnership on was Zico Coconut Water. And, uh, yeah, I think this is interesting 'cause now we're seeing a pattern. The first is you're picking businesses in like categories that they're not in the MBA 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 that 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? Very few people are even thinking about that niche. It's not common. Then you go coconut water. So now you're, consumer packaged goods in a beverage category that's nonexistent really at the time. And I think Zico was pretty small when you found it. It's not like it had like, you know, tons of momentum. So talk about two things. Number one, finding these niches, like what, what is it that you, what is your operating philosophy that leads, that seems to consistently lead you to these? That's the first question. And the second is the key partnership that got it off the ground. I heard an amazing Matt Damon story. I want to hear the full version of it.

What was Z-Cup?

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 stores 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, 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, 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 a 980 on my SAT. 'cause 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, um, was friends with one of my customers at Marquis Jack. He got me a meeting. I pitched the meeting, uh, in the meeting I pitched this idea of coconut water. He takes a liking to me, but he says, We don't buy PowerPoints. We're Coca-Cola. We buy brands. He goes, but if you partner with another company or something, you know, maybe we can then out 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 in, we'll partner with you. So I went to Zico and that's how we formed the partnership during the meeting. The, um, 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 Kopelman 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 two. 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. He's like, I love coconut. I have a coconut tree in my backyard. He's like, I drink Coke. He goes, if anything happens, what, you know, with this company, let me know. I may want to 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 outta nowhere, like I know I had to change the whole energy feel of the meeting. Yeah. I just turned to the president, the guy at Coke, and I'm like, you know, my partner Matt Damon and I, and the guy went, Matt Damon's your partner? I said, I didn't mention that. What are you talking about? We go all the way to the 1-yard line. I leave and I call Matt. I'm like, Matt, I need a favor. He's like, I'm like, can I come over with the cat? Can we climb up your tree, get a coconut, chop it open, you know, go in the kitchen, put a straw in it, you know, 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, All right. And 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, and we got the deal. And the cra— you know, what's interesting about that is obviously who's gonna get, you know, a, a megastar to come. It, that's not the point. It's, it goes back to what I said. Um, 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 meet, making yourself stand out and be memorable in a meeting. Now I stretched it a little with this one, but, but, um, but it ended up, it ended up working out.

That's an amazing story.

That's amazing. That's a good one. I love that story.

I love that story.

You, that's wild.

By the way, Coke bought it 2 years later. 100%.

Did you, uh, when you bought, did you buy into Zico at the time? Like did you, uh, Was that like a—

Yeah.

And have you made bets that you felt like financial bets that were risky? Like, you know, Elon does this thing where he sort of rolls all the proceeds into the next business and sort of re-goes all in each time, which is, you know, probably not advisable to most. But like, what's your strategy been now that you have some chips to play with? Do you— do you make big financial bets? Are you saying, no, no, I'm going to add value strategically? Do you start things from scratch? What do you— what do you like to do with the chips that as you accumulate them? How do you, how have you used that to, to your advantage?

Well, I've, I've realized that I've got, as I've gotten older, that more isn't better. Better is better. And I really don't make a lot of bets. I have 4 kids. What I'm most proud of, Sean, in my journey at 55 is that I've been, I've, I've exited 5 businesses, but I've been able to keep, build a family, keep my health, you know, be a really good son to my parents. I have great friends, so I really aren't, I'm not, and I'm not using Elon as an example. You, you brought him up, not me, but I'm not trying to roll everything in or I'm really proud of what I've been able to do and I, I'm really proud of the life that I built. So I really don't, I really say no to mo— I have this thing at this point in my life, if it's high aggravation for high reward, I'm not doing it.

If it's—

and that goes for anything, money, friends. I don't want high aggravating friends. I'm on friend reduction right now. I'm on friend reduction, man. I want low aggravation.

You're doing layoffs? You do Zoom calls with people, let them know, hey, I'm sorry, we had to make a reduction in, in friends.

We're doing layoffs here.

Excuse me, Mr. Damon, can you step out of my office?

There's a severance package. We'll hang out 3 more times, but then that's it.

We need to have a discussion. That's great.

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

What was it?

I wanted to take commer— this is going back 8 years ago, so now it might sound like Oh, well, people are doing it now. I actually pitched this to a major airline now, um, that's doing it, but I wanted to make commercial travel feel like private travel for people. I felt like there was a bit, and there still is an opportunity for people that would pay up to fly commercial, but they want an experience that's more private. So for example, if I'm flying from New York to California, and I'm by myself and I'm on a Global or a Gulfstream and I'm going round trip, that's an expensive flight, man. That is an expensive flight. Where I could just buy a first class ticket for maybe $1,500. So instead of, let's say that that flight cost me, if you chartered it, maybe it's gonna cost you, let's just say $50,000. It might be more, it might be, I have no, 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. I, as a $1,500 ticket holder, would gladly give you another $1,500, United American Delta Frontier, whoever, if you could walk me through a back door and make me feel like Mick Jagger and escort me onto the airplane through the back door. And, um, no one was doing it. No one was doing it, and now they are doing stuff like that.

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

Because once you get on an airplane, do you really care?

Yeah, it doesn't matter.

I'm in 1A, no one's bothering me in 1A.

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

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

Well, you, you, but you can't turn that switch off, right? Because I saw you on Instagram. Like, you know, I don't know, a year ago or 6 months ago or something like that. And you were like, pickles.

It's—

and you were like, uh, guys, pickles. And, you know, it seemed like, you know, the guy who was saying coconut water when nobody was talking about coconut water, he's talking about pickles. So me and Ben started paying attention. We're like, hey, what's Jesse Itzler doing with pickles? Well, okay, he's kind of right. There's no brand in pickle. And 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. Yeah. What do you see in the pickle market?

Well, like 245 million Americans eat pickles every year. It's like 75% of our population eat pickles. And again, it goes back to the, to our running conversation. I'm starting to see at races, pickles at the, at the, at the aid stations. They never existed 10 years ago. Pickle juice never existed 10 years ago at, at the aid stations of marathons and your local 5K.

To help you with running.

Now they're popping up. Yeah. So that made my antennas—

it's, what is that? 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.

Oh yeah. In Russia it's a, it's a, you know, it's a big remedy for hangovers. But my point is like, it, 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 100. I'm gonna, so, so I started doing, so I started thinking about it and I'm like, you know what? I can't even name 3 pickle companies. And I, I love pickles. I don't even know pickle 3.

This is, by the way, this is the part where he is gonna bring in a focus group of 10 people and he is gonna say, name a pickle company and nobody can do it. And he is gonna be like, that's the business plan.

Well, listen, so I, I, I researched like the 7 best tasting pickles. And of the 7 best tasting pickles, I think it was like, the Today Show did or something, you know, it's like, it's like someone credible did it. I only knew one cup, one of the companies. So I'm like, if I only know one of this top 7 best tasting pickles, there's a problem in the marketing of pickles. It's a marketing problem and I'm a good marketer. So, and it, that's where it started. And 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.

I, I'm a, I'm a pickle guy too, Jesse. Same.

Is it Claussen, like the big brand? Is that right?

I like Claussen. I like Mount Olive. Is it called, uh, Valsic or Va— Vlasic? I, I like that company. But I think Mount Olive's is the biggest ones. I always get the little ones that look like a witch's toe.

You're wearing a metal pickle shirt.

I'm not like—

I'm not—

I'm not big.

This is a big pickle.

Around with a Claussen. No disrespect to that company. I don't even know. But I'm just saying, like, you ever seen anyone wearing a hat? Just, oh my God, it's like—

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

Why do that? Let's just— let's get the Beast on the phone. Let's partner with the Beast. Beast Pickles.

That's right. That's right. Who needs Matt Damon? We got Jimmy now.

Mount Olive. Yeah. Where's David? I need to go get Ben Affleck. He seems like a good pickle guy.

I need to know about Beast's low aggravation, though. I only want the low aggravation partners.

Yeah. Well, I don't know about that one.

Mount Olive does $220 million in revenue a year. Privately owned.

It sounds— it sounds doable, man.

Sounds like our money. Right, guys?

Yeah.

Yeah.

I want to thank them very much for holding it for us. Yeah. Shoot a text over to CEO of Olive and just let him know to keep that money warm for us. All right.

We'll be there soon. What other ideas you got? Because I told you, I said, you know, you'll get this because, you know, you're a rap guy. When you go on certain shows like The Breakfast Club or Sway in the morning, there's like an expectation. Like, okay, if you come on here, you got to freestyle. And we're trying to do that of 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 go, you tell me, you go, I got 50 ideas in my top drawer. And I said, all right, say no more. But you hinted at me.

By the way, uh, the, the, the pickle names sound like a rap name. Sweet Gherkin, Bread and Butter, Kosher Dill. Like these are all rap names, man. Yeah.

Yeah. Yeah.

We're about to have Migos pickles. All right. Tell me, tell me about this idea. You, you gave me 3 words. I don't know what the idea is, but you said ready-made 8-ounce drinks. What, what you got in mind?

Yeah. So I mean, I, I've been accumulating ideas in my, in my top drawer for 35 years. I love starting things, Sean, you know, but yeah, that, I mean, I don't, I don't mind. By the way, if you guys wanna run, anyone wants to run with this, you can. I'll take a one penny royalty and 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 shrunk it down to 2.5 ounces, right? That's what 5-Hour Energy was. And why did it work? They, they only, I believe, I believe they only 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 it was like on the countertop at checkout, impulse buy. They were selling 10 million 2.5 oz bottles every week. 10 million. 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 this, that. 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 self-stan— 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, and other retailers. And I think there's a tremendous opportunity. I was gonna call 'em quickies to have like ready-made shots. Same thing as, as Five Up, 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, et cetera. 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— here, now you got me thinking, Sean. Now I'm like, this wasn't even on my radar, but here we go. Like the freestyling that you were talking about on explain the tech. 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 chain of liquor. I mean, like, you go into your local liquor stores, like the guy, my neighbor owns a liquor store. I go there and I 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. You want to put your widget there? You want to put your fucking widget there? Keep the money warm, son.

Yeah.

Keep the money warm.

Oh, I love it. Yeah. About real estate.

Probably 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 bad idea. Oh, better idea. The idea.

Yeah, yeah, exactly. Exactly. And, uh, you, you're kind of like, I think the background of rap, I'm not, I'm not joking about this. I, I think the, the way the brain can sort of like not censor itself and wait till it has a fully formed perfect idea, but actually just start to go and then know that, oh, I'm gonna hop from this to this, to this, to this, and there, that'll be the line. And that's all I need to do is get to that one, that one line.

I'm gonna show you this too. This is, this is something I'm selling now. This is, I don't know if, are we on, are we just talking?

This is on YouTube too.

Are we on?

Yeah. Only here or no? No.

Or video.

Video.

Video.

There we go. This is my 2024 all planned out. This is next year, fully, almost fully baked what my year looks like. My races, my, what's orange?

There's a lot of orange on that. What does orange stand for?

Orange. Orange are, so when Sarah sold Spanx, she wanted to do a lot of traveling. So 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.

Yellow. What's yellow? What's yellow and what's, what's green or blue, whatever that is?

Yellow are my races and events. Green is my speaking. Uh, green is, oh, birthdays, this stuff.

This thing's dope. I wanted to ask you about this because you are super legit as far as like what you've actually been able to accomplish. Your level of success and you do stuff like this, you have like the Big Ass Calendar Club or whatever. It's like that thing is called Big Ass Calendar. That's a product you make. It's like a course you have. And I'm always surprised that you're doing those things. And you know what? What's your thought process on like—

or the running club or the running club?

Like, how do you pick projects?

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?

34.

I'm 35.

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. You're the forties and fifties. Thirties, forties, fifties. You know, for me, there's, I'm in, I'm in a coaching space. You know, um, um, 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's, 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, um, the gal who works with us in our family office was looking at all the businesses and and asked 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 wanna scale this? And what are you doing? Why don't, why don't you just go do the liquor idea or the airplane idea or this idea or that idea or any of the ideas in your drawer? And I pulled out my phone and I said, Kendall, all these are from today. All of these messages are for today. Pick one. 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's 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 'cause I sold 5 of 'em. 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 are 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 want to do that, man. I did that.

So a question that we like to ask people is, it's a really simple question, but we learn a lot, which is like, what do you do with your money? So like, you have a really interesting lifestyle. I agree with you. I'm not, I don't like the Elon Musk path of all these sacrifices and doing things for the sake of humanity. I'm like, I'd rather have a fun life. And you have a really sick life. I mean, I'm a former college athlete runner. So I like watching what you're doing and I like to work out and do these podcasts and have a lot more fun than just work. What do you do with your money? And when you're financing this, are you just— are you using your speaking fees to finance it? And then 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?

Well, just, you know, it's, um, I don't know, man. Like we, we, 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. Like we don't really think about it. It's like, it's spread out strategically and we live our life.

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

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. What, whatever that costs me, Sam, is what I'm gonna spend on it. How's that for an answer?

Yes, Sam.

I still love you, Sam.

Uh, I wanna ask you about something that you have talked about that I really liked, which is, uh, around your life philosophies. So you have a few of these that have made an impact on me. You, um, I don't know where I saw it, some TikTok clip or something. You were talking about like this 3-minute daily thing. You go 3 minutes and I forgot exactly how you phrased it, but it was like, compli— you go, I can network in 3 minutes, right? I can, I can invest in my friends, my fi— my network in, in just 3 minutes a day. And I'm always interested in anything that's like, you know, the 6-minute abs. I, I, I tend to be interested in the, like, you know, shorter timeframe type things. And do you go compliments? What was the other ones?

You go compliments, um, complimenting, congratulating, consoling.

Explain that, that philosophy. Cause I've been doing that now where I, I basically go through my text list and I'm like, who's somebody I could compliment? Boom. Send it out and they love it cuz they're like, uh, 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 like kind of like a, a actually like a very effective little tip I want you to share with here.

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 went 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, it's a great way to get through the, the clutter of email, DM, social, you know, all this stuff. 'Cause 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 K Academy, Coach K. I have sent a, uh, fluent to Carolina. not too long ago, and I sent Coach a text thanking him for having the event. And I said, you don't even have 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 don't know if you got it, but like, I had that permission to do it. I'm not coming outta left field like, oh, hey coach, you know, like, whoa, you just— so that took me 45 seconds to hit send, write it and hit send. 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, inflip, whatever, over the course of a year, I'll send 1,000. I will plant 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 'em up, I just fire off a couple of emails or call 'em or whatever. So that was that theory. The compliment, congratulated, consoling is really just kind of 3 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, that they— 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 want to console the people that if, you know, something happens to a friend in your life that's great, you wanna congratulate 'em, 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, you know, I, you just call someone outta nowhere.

You default to calls or texts either way.

I just think I personally like handwritten letters. Here's one. Um, because I feel like the intent, it takes a little longer, but to actually get a stamp, lick it, go to the mailbox, put it in the mailbox, it's received completely different than just sent. But you know, so if I would like in the pecking order, but you don't have the ability to do that, 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 close out the year process that I kind of teach people, but like, and that's one of 'em, you know, but you compliment, you gratulate, you console, and you do that to people. And like, if I, Sam, if I hit you up, God forbid you had something bad and, and, and I don't even know, I just met you for the first time. Other than the question about how my burn rate, I love you. So if I, if I were to call you up after one meeting and say, Sam, man, I heard about XYZ, man, I'm so sorry that happened to you. And then 4 months later I call you up and say, Sam, man, you guys just hit 5 million downloads a day. Congratulations, man. And then I call you up again at the end of the year. I said, Sam, I just wanna let you know, man, that question you asked me about, about my burn rate, you know, I rethought it and I wanna compliment you because you asked the tough questions. And you know what? That's the seat that you're in. And I give you credit for asking questions like that to people on the other end. And I really admire you for that. I do those 3 things in that year, you're gonna think differently about it.

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

All right, well, bad. Sean, you laugh about that, and we're laughing about it, but let me ask you a question. Who doesn't want to be a hero?

You're right.

Who doesn't want to be a hero? We— like, 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, like You know what, I built my career doing that.

Well, so this is about relationship, but you also have others about skill building, life experiences. Explain some of your other kind of life rules, cuz I think these are really worth sharing. Uh, you know, people I think will be entertained and inspired by the business stories, but my hope is that that actually was just buying the right to drop a little wisdom on 'em at the end here, cuz this is the stuff I've liked the most from you, from your story. Um, so, so tell, talk about, you know, the sort of misogyny or the, The Kevin's Rule, like these are pretty foundational.

Yeah. Well, that goes into kind of the planning that I showed you on the calendar. And, um, I really do, do 2 or 3 things every year. Um, 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 a SEAL, the book I wrote. 2017, I lived on a monastery. 2016 or something, I started 29029, 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 one, or the way I've interpreted it is you do one big year-defining thing. and you had, you should have something to show for it every year. By the way, if you're 35 years old, I don't wanna, I don't just rounding up here, um, 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. Um, which is every other weekend I do something I normally wouldn't have done. It's 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, um, watch some, spend a couple hours learning something I, I didn't know. Um, I coined it Kevin's Rule because Kevin and I were camping at Mount Washington with our kids and it was like, I 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, Kev, there's 8 billion people in the world, man. It's only us on this mountain. You know, it, how often do you do this? 'Cause 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. And I'm like, well, 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, man, 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 here 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?

We have a rule here. We don't do public math, so don't worry, you're off the hook.

Okay.

There we go.

That's a great run. That's a great run.

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. And you have this similar quality where you just have a framework and you know what you like and you stick to it and you're really intentional.

And I appreciate that. You live life on your terms, which is what I think the highest calling thing we respect on the pod is somebody who defines their own terms and then lives on them. Even if you don't, even if somebody doesn't agree with you.

Because even successful people don't do that. Like even people who are wealthy, they're like, I fucking hate my life because I'm tied to this job that I actually don't like doing. And you're a great example. Your, your, your, your definition tends to be exciting and awesome 'cause you do all these adventures, but it doesn't matter what your, your definition of, of like your framework is. You've done a cool job of defining it and sticking with it. And I appreciate that.

Well, one cool thing that's different is Rob's is all about maximizing he's like efficiency. How much, how do I use my time? How do I allocate it? And how do I get the most done in that time? Whereas I feel like Jesse's almost like, it's a different relationship with time. It's like, how do I have the maximum number of, of incredible experiences, um, and amazing relationships and moments, whether that moment took 5 seconds or, you know, 5 days or 5 weeks, it doesn't really matter. It's like maximizing kind of like squeezing the juice out of, out of the fruit. You know, versus, versus, uh, you know, trying to optimize every moment.

In, in a, in a, in a generation of hustle and grind, which is so obvious, no shit, you gotta work hard. That message gets lost and you don't want to give up your 20s and your 30s and your 40s and certainly not your 50s if you can avoid it. Just grinding and chasing something that you can get the same feeling. Doing something else.

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

And, uh, that's the pod.