My First Million - Jesse Itzler's Exact Playbook For Creating HIT AFTER HIT

Episode Date: October 5, 2023

Episode 504: Shaan Puri (https://twitter.com/ShaanVP) and Sam Parr (https://twitter.com/theSamParr) talk to Jesse Itzler (https://twitter.com/jesseitzler) about how he turned $118 into massive businesses including Marquis Jet and ZICO coconut water. Want to see more MFM? Subscribe to our YouTube channel here. Want MFM Merch? Check out our store here. Want to see the best clips from MFM? Subscribe to our clips channel here. — Check Out Sam's Stuff: • Hampton - https://www.joinhampton.com/ • Ideation Bootcamp - https://www.ideationbootcamp.co/ • Copy That - https://copythat.com/ Check Out Shaan's Stuff: • Try Shepherd Out - https://www.supportshepherd.com/ • Shaan's Personal Assistant System - http://shaanpuri.com/remoteassistant • Power Writing Course - https://maven.com/generalist/writing • Small Boy Newsletter - https://smallboy.co/ • Daily Newsletter - https://www.shaanpuri.com/ — Show Notes: (0:00) Intro (4:30) $10K for 10% of your life (7:30) Can vs Will (13:30) Going from Jingles to Jets (17:30) Jesse’s underdog mentality (23:00) Marquis Jet: The craziest origin story of all time (32:30) How Marquis Jets worked (36:30) Getting celebrities as first customers (43:00) Zico: Finding profitable super niches (50:00) Business Idea 1: Private travel experience for commercial travelers (54:00) Business Idea 2: Pickles! (58:00) Business Idea 3: Quickies-Ready-made 8oz Drinks (1:02:00) Jesse Itzler's Philosophy on Money (1:08:00) Jesse Itzler's Philosophy on Relationships: Compliment, Congratulate, and Console (1:08:00) Jesse Itzler's Philosophy on Defining a Year — Links: • Jesse Itzler’s website - https://jesseitzler.com/  • New York Knicks theme song "Go NY Go" - https://tinyurl.com/9yfach3r • Living with a Seal - https://tinyurl.com/wdjkj2je • Marquis Jet - https://www.marquisjetset.com/ • All Day Running Co. - https://www.alldayrunningco.com/ • Big A## Calendar - https://tinyurl.com/22ujummp • ZICO - https://zico.com/ • Sara Blakely - https://tinyurl.com/6ye642w4 • SPANX - https://spanx.com/ Past guests on My First Million include Rob Dyrdek, Hasan Minhaj, Balaji Srinivasan, Jake Paul, Dr. Andrew Huberman, Gary Vee, Lance Armstrong, Sophia Amoruso, Ariel Helwani, Ramit Sethi, Stanley Druckenmiller, Peter Diamandis, Dharmesh Shah, Brian Halligan, Marc Lore, Jason Calacanis, Andrew Wilkinson, Julian Shapiro, Kat Cole, Codie Sanchez, Nader Al-Naji, Steph Smith, Trung Phan, Nick Huber, Anthony Pompliano, Ben Askren, Ramon Van Meer, Brianne Kimmel, Andrew Gazdecki, Scott Belsky, Moiz Ali, Dan Held, Elaine Zelby, Michael Saylor, Ryan Begelman, Jack Butcher, Reed Duchscher, Tai Lopez, Harley Finkelstein, Alexa von Tobel, Noah Kagan, Nick Bare, Greg Isenberg, James Altucher, Randy Hetrick and more. — Other episodes you might enjoy: • #224 Rob Dyrdek - How Tracking Every Second of His Life Took Rob Drydek from 0 to $405M in Exits • #209 Gary Vaynerchuk - Why NFTS Are the Future • #178 Balaji Srinivasan - Balaji on How to Fix the Media, Cloud Cities & Crypto • #169 - How One Man Started 5, Billion Dollar Companies, Dan Gilbert's Empire, & Talking With Warren Buffett • ​​​​#218 - Why You Should Take a Think Week Like Bill Gates • Dave Portnoy vs The World, Extreme Body Monitoring, The Future of Apparel Retail, "How Much is Anthony Pompliano Worth?", and More • How Mr Beast Got 100M Views in Less Than 4 Days, The $25M Chrome Extension, and More

Go rent the countertops of all the liquor stores and then go to an abysco, one of the big boys, and be like, hey, guess what? I don't want to put your widget there? You want to put your fucking widget there? Keep the money warm. Yeah, keep the money warm. Yeah. I feel like I can rule the world. I know I could be what I want to.

I put my all in it like no days off. Okay, everyone, what's going on? This is Sam. We have Jesse Itzler on the pod today. Very fascinating guy. He started a bunch of different companies. The biggest one being Markey 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. We went deep into some of the numbers behind some of his businesses. We learned about his early career. And there's, like, a ton of takeaways. 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 is super fascinating. If you like the Rob Deerick episode, which a lot of people did, I think our most listened to episode of all time, I think you're really going to like this one. It was pretty spectacular. I love feeling good 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 of 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 two. 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. All right. Well, welcome. We got Jesse Itzler here. also known as, I think you might be the richest runner, white rapper in the country. So congratulations, my friend. 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, then have four kids that eat plant-based, et cetera, et cetera. 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 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 sports teams. ended up selling that, then created Markey Jets, a fractional jet owning company, sold that to Berkshire Hathaway, which Warren Buffett, obviously

he runs and owns. You're married to Sarah 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 was when I read Living with a Seal, which is the story of you living with David

Gagins for 30 days. I can't even really listen. I gave David Guggins for 30 minutes on a podcast, So living with a 30 days, respect. And yeah, you've created a bunch of companies outside of that, partner 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, humble beginning.

So talk about the early days when you were, you were trying to do the, let's start with a jingle company. You told me you were sleeping on couches at the time, trying to make it. And describe kind of what was going on at that time. And what was the plan and what were you going through? 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 at a bigger way. And that was the intersection of that happening and me going to college.

So 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. Like, why would I waste my time making a resume? I want to make an album. So it was like kind of asking 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 met, like, I wasn't super connected. I didn't have like a lawyer. 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, try to make it. And somebody offered you a tempting deal. They said, 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 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 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 SPAP. So I needed money to fund that production. So a music manager said, you know, I believe in you. I'll give you 10 grand for 10%, but I want to own you for the rest of your. your life, basically 10% of anything you make.

And I was like, I'll take it because I needed the money to go with this. I thought it was a deal of the century. You're going to give me 10 grand. And all I'm going to 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, uh, 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 emergency, 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, it's an emergency, you can come live with my roommate and I. Monday, my friend kicked me out because 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. You owned the company called Kinney Parking garages in New York. And was, 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 she said me on, by the way, his name is Lou 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. So I went to, not to believe by this, but I went to see him.

And it's really relevant for anyone listening what he said to me, as a 22 year old. I told him my dilemma, I'm going to 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 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 said, will you, son? And I said, yeah, well, 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 blew that flame into me at an early age. And it's really been a theme throughout my life and all the buckets of my life, the whole will versus can notion, you know. And why is that so powerful, the will versus can't? Well, because it really puts the pressure, you know, Billy Jean King at a book, pressure is 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 going to know unless I sign up for the race, put myself in a position where something incredible can happen or not. But I got to put myself in that situation. And now it's up to me, like, will I get it? done. You know, what am I willing to do? Am I willing to suffer for that one day for to have the next

three decades have that in my memory bank and have it on my resume? And I am willing, and I am willing to do that. And I did. So you know what's really funny? 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, this, you have any good stories. And you told me this, this Wilvers 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

I thought 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 did 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 ask it to be can? We don't ask can questions anymore. As of meeting Jesse Hitzler, 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 say something that you've done like, you know, I did, you know, rim to rim, I'll take physical activities, or I climb Kilimanjaro, and you explain to someone like, oh, I can do that. And I, 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 just 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 don't know about. So you used to go to something, at least you went once, called Coach Kay's Fantasy Camp. Is that correct? I've been there for 18 straight years. Okay, perfect.

So you went to this thing. So those who don't know, Coach Kay, he was the greatest college basketball coach at Duke. I went to Duke and my roommate, Trevor, used to volunteer at Coach Kay'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 going to 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, 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 cost 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 was all he was doing was driving the shuttle back and forth between where y'all were staying and the thing he's like dude it's amazing he's like just hearing these conversations

what they're talking about in this like nine 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 a hundred bucks for this like 10 minute shuttle ride. And he late, I told him, I told, I was mentioning to him that you're coming on the pot. 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. And we needed to convince this famous chef in L.A. 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. into the trajectory of our life. So little did you know. I love that. And yeah, I've been going there since I'm 35. It's for guys 35 and older. And it's not to chase 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, times undefeated. It's always ticking. it's the six days a year or the five days I go there

that I get to feel like an eight-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 eight-year-old a lot of times. I'm pretty sure I just.

I do, I do, I do. I shouldn't say that. I'm pretty sure I just saw you like in an RV with like eight friends just like running around the country. It seems like you, yeah, it seems like you got the eight-year-old life kind of nailed down. I like to give myself that excuse, Sam. I guess you put your right.

It's more than once more than five days a year. Yeah, I think I think you've done that all right. You, uh, and then was your first, um, kind of major business, Markey 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 that. I, I, bubble gum is like bubble book gum company that no one ever heard of like just anything that our podcast intro needs a little spruce it up if you want to if you want to dust it off yeah i i got you guys and um and then i start and then one of those jingles gave me an opportunity to write a theme song for the new york nix i had done a a commercial a radio ad for a company called in the in the pain clothing

it was owned by um nancy grunfeld ernie grunfeld the gm of the nix wife And she really liked what I had done. And she said, yeah, if you have any other ideas, you know, let me know. I said, well, I 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 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 grand to say they were my customer. Because once I had the Nix, those phone calls to get into the other sports teams became very easy. And that became my calling card. So I built a business around that, Sean, that actually I ended up doing theme songs

for almost every professional sports team and turned it into a business where we were selling CDs, like 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 million.

And then 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 on the first $4 million,

I made like a million and a half. 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. A million and a half dollars. I would go to the, wake up at the 8 and go to the ATM.

I would get 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 dollars than I had yesterday and I was sleeping I'm like I'm going back to bed I'll go back to bed

my partner convinced me to take all the money my partner convinced me to take all $1.3 million that we both cleared after taxes or whatever it was and reinvested to to get like exclusive deals in all this

like we made the business being reinvested it in the business business and actually made the business a lot bigger. We got our earn out. And then everything changed a little bit for me. But, you know, I had no idea to manage money. My parents never talked about money. My dad owned the plumbing supply house. My mom raised four kids. 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 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. 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're going to 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 dollars year one, $20,000 year two, year three was $50,000. Year four, 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 two or three years to accumate, uh, and kind of get used to and learn what to do. But there's no one to teach you. The problem is I, I'd always been taught. Oh, if you're a millionaire 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, man. So I was 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.

I'm a big believer that most of life, most of your life kind of 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 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 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 because, 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. 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 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 cleaned meat troughs. That didn't work. I sold chicken, shrimp, and meat door-to-door. That didn't work. I mean, a jingle company. It went on and on. So, you know, I had really worked so hard.

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 such a driver. 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, one of you guys were 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 salesmen than me. but I love that feeling of I got to 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 got to catch Starker, you know. The Markey Jet thing, that's interesting, though, because that's like totally out of left field. And that seemed like a way bigger win than the jingle business.

Same partner, right? Same co-founder. Yeah, same partner. It was a much bigger win. And like most things in my life, most of the businesses that I've been involved with weren't planned. And most of my successes in life haven't been in my business plan. They've been opportunities that presented themselves. You know, my old life I've been taught when opportunity knocks, you know,

and I'm not, I don't want to sit around waiting for opportunity to knock. I like to create 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 it led to some research. Like there's only really two or three ways to fly privately back in the 90s when we started Marquis 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, being a fractional program like Net Jets, but even that is a really, really big commitment, both in capital and time. It's a five-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 want to fly like 25 hours a year. I bet there's a lot of people like us that don't want to own an airplane, don't want the responsibility, but they just want to be able to have have a plane available on short notice. And that was the idea around selling a 25-hour jet card that worked like a debit card.

So if you and Sam, Sean, flew two 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 and my life, many times it's been through partnership. We partnered with NetJetts.

They ended up buying us to use their airplanes. partnered with Coca-Cola at Zico-Cocan order. They ended up buying us. But anyway, 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 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 then started that journey of building this company. So you walk into NetJets and you're like, hey, 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 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 multi-billion dollar company let two kids that didn't break a thousand on their SATs into a room to pitch them the idea? A year before that, I was a yes guy my whole life. I was I 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 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 has 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 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 do. but you lit my daughter up and if you ever need anything, let me know. It turns out, I can't make this up. He's the president of the Chats a year later. I need 650 airplanes.

I'm like, Jim, you're never going to believe this. The guy who's 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 party, he doesn't give anyone 12 minutes. He goes, there's 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 can never sell them in a PowerPoint, which is like what everyone, guys sees 100 PowerPoints every year. We brought in our own focus group. We'd eight people in the lobby, and they walked in one by one. And they stood up and said that they would never buy a fraction of an airplane what net jets 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 couple of years later we had more customers than net jets 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 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. 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, the MC was there, was right behind me on the wall. You know, when these guys at that meeting, yeah, we brought it, we brought them in. We brought them in. And when we said when 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 much older corporate client. And 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 buying into people 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 going to 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 asking us, 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 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, Penny and I, my partner and I that he wanted a 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 today, but I got it now.

You know, like I said, that was never in our business plan. Oh, we're going to 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 business plan that make the biggest difference. And when you have a chance, you know, you don't get a lot of big meetings like that. And I remember 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 is 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 fortunately, we were able to do that. And it worked. And then we had an amazingly fruitful relationship and partnership with NetJets until we exited. Are you, so like I think that all three of us might be a bit similar

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 going to 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 Instagram.

I'm not so good at the, now with Instagram, but back when there was no Instagram, I was good at creating pirable opportunities and, and talkworthy 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, five 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 membership?

No. So we, the original deal with Netschets 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 by 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, we have 4,000 members. We're doing a billion dollars 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 those headline numbers are really big. How big was that exit? I mean, that's a pretty big thing. How big is Net Jets?

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? NetJest sold it to Berkshire prior to us. And then we went to now we're part of Natch. Mount Cheettschette's now part of Nets. Does your Berkshire stock?

Because that would have been a good stock to just get in the deal. I know, right? No, we didn't. NetJets sold for $725, $725 million in 98, and half of it was paid in stock. So that was a good deal for net Jets, depending on, I don't know what the revenue was, but that's a lot of money. 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 would be insane. No, it is. Yeah, no, because our average, our average customers spent close, I think it was $250,

or $235,000 a year. Gotcha. Okay. But it's more like GMV. So because you have to, so your take is some spread between that and then whatever that's, okay, gotcha. So, yeah, I guess like on that model, what's the income on 200, let's just say 100 million? What can your profit be on that?

Well, this is 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 very good life. 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. You told me something which was about getting the first customers. So before your wife was even a customer, 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 huge, like, where did you go find those customers and tell the story of kind of how you got it off the ground? Well, we started out, you know, I think the first thing that any entrepreneur, most entrepreneurs, at least in our position,

and at Marquisa, is we had to establish 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. And I said, oh, my dad and my next door neighbor, you probably would leave. 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 10. So I flew out to Monterey and, you know, I told the guys like, hey, I'm going to go get my first sale. I'm going to the thing called the TED Talk. They were like, what? He's Ted. It's in Monterey, California. You can't even get there.

You have to, like, connected through Chicago into whatever, rented a car, five hours of 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 going to sneak in, buy someone's past? like go into the room where all the qualified leads are.

I'm in this coffee shop plotting like, you know, my entrance or how I'm going to do it. And every two hours a weave of people come in and they're buying, they have these credentials. 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. Laties and muffins. So the next morning I got up at five 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 been verified. You can walk. So two hours later, this got the first wave of people on the break walking. And the guy orders a latte and a muffin. I stop them. They tell them that they could give them a latte, but they're all out of muffins. It's like fucking nine of the morning.

He's like, you're out of muffins. The guy starts walking. I stop him. It's sorry. I overheard you. I actually have an extra muffin if you want a muffin. And he's like, you got an extra muffin. And I'm thinking like I got every single fucking market under the table, man.

What do you need? And I started talking to him. He's like, you know, what do 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 got to be kidding me.

I'm in the market for a private jet card. And his name was Josh Coppom and he owned the company called Half.com. Famous VC. Right? Now he is. I bumped into like three 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 Ken, of putting myself in a situation where I could attract that kind of luck, you know? And 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 them. 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 EM, DM and all that. Of course, I did what everyone he would do. But he went to Mexico. 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 at every night at 8 o'clock during spring break in Mexico in case he and his wife wanted to go a dinner. And, 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 five years until we grew this. So no, I was never the CEO. I was never the, the, the operator.

I was never the C-O-O. I was, I wasn't even, I don't even think I was on the or chart. So 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 2005 version of MarkeyJet.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 because Ken Austin, I see, was your executive VP. Is that the same Ken Austin that went and started, is it Avion, the tequila company? And most recently started proper 12 with Connor McGregor. 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 were the Boston Celtics. We, from like the old, we, the talent at this company was exceptional. Ken Austin is an exceptionally, I don't, he could be the, he's such a talented guy. And 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. You're like, oh, you're here at this jet company.

So I know like you're of someone. I know you're someone interesting. Definitely. Just so it happens. I work here or I own the company. I mean, it's like a, that'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, some... Including Garrett Camp, the guy from Uber. He tried to do an Uber for jets that didn't work out, right? It's very, very difficult.

And if we didn't have net jets as a partner, you know, I'm sure it wouldn't have worked as well. So a lot of things lined up for us. The business you did a partnership on was Zico Coconut Water. And I think this is interesting because now. we're seeing a pattern. The first is you're picking businesses in like 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 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? It's 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 non-existent really at the time. And I think Zika 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 is it that you, what is your operating philosophy 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 Zika? 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. Let's try to figure out. This is, there was no coconut water in the store's time.

This is, so let me back it up even further. I was running a hundred mile race. And I did a lot of, when I was doing my training, I did a lot of research around hydration and nutrition. If I'm going to run for, arguably 24 hours. How many calories do I need to eat it, 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 going to 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 needy 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 then out that's out there that's prove 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, about a week before, I was at Matt Damon's house. And Matt was also a customer of a marque jet. And I did the things that I did for Josh Coppulman 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've got to be kidding. He's like, I love coconut.

I have a coconut tree in my backyard. He's like, I drink. He goes, if anything happens 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 this PowerPoint, you know, like, and out of nowhere, I know I had to change the whole energy feel of the meeting. I just turned to the president of the guy at Coke, and I'm like, you know, my partner, Matt Damon and I,

and the guy, Matt Damon is your partner? I said, I didn't mention that. What are you talking about? We go all the way to the one yard line. I leave and I call Matt. I'm like, man, I'm like, man, I need a favor. I'm like, can I come over with a 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 Moutar, Moutar Kent, the CEO of Coke, there's got to 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 got to be a better way. And we got the deal. And the creak, you know, what's interesting about that is, obviously, who's going to get, you know, a megastar to come? That's not the point.

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. That's an amazing story. That's amazing. That's a good one.

I love that story. I love that story. That's wild. By the way, Coke bought it two years later. 100%. Did you, when you bought, did you buy into Zico at the time? Like did you, 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 regos 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 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 like to do with the chips as you accumulate them? How do you, how have you used that to your advantage? Well, I've realized that 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 four kids. What I'm most proud of, Sean, in my journey at 55 is that I've been, I've exited five businesses, but I've been able to 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 brought them 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'm really proud of the life that I built. So I really don't, I really say no to most. 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 a 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 France. We're doing layoffs, here. Excuse me, Mr. Damon. Can you step on my office? There's a severance package.

We'll hang out three more times, but then that's it. We need to have a discussion. That's great. It's so fun. But I'm not trying to, you know, push you really. It's like it's based on my enthusiasm for something. How's it going to impact my life, meaning like day to day. I walked away from several ideas that I think could be really good.

Just because you have a good idea doesn't mean you should do it. And Sarah said that to me. I had an idea now. I see people are doing it now. About eight years ago, I said, Sarah, I have an idea that's bigger than Marquis Jett. Like Marquis Jet was the biggest thing I'd done, you know? And I walked you through it and she goes, that's an incredible idea. Don't do it.

What was it? I wanted to take commercial. This is going back eight years ago. So now it might sound like, oh, well, people are doing it now. I actually pitched this to a major airline now that's doing it. But I wanted to make commercial travel feel like private travel. for people. I felt like there's 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 a 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 going to cost you. Let's just say $50,000. It might be more. It might be like, 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 $500. I, as a $1,500 ticket holder, would gladly give you another $1,500, United American Delta the front of whoever, if you can walk me through a back door and make me feel like Mick Jagger and escort me onto the airplane through the back door. And no one was doing it. No one was doing it. And now they are doing stuff like that.

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. Why do 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, but I've been on a, I flew first class from New York to L.A. one time for like some meeting. I had never flown first class, but I did it because it was overnight and I had to be ready for a meeting. And I get on, I was 1A and 1B or sitting there next to me with Stephen A. Smith. And I was like, how the fuck do you go 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. 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 I'm involved with some NBA players

and I'm part owner of the Atlanta Hawks. And so I have, I have, and my friends are all doing really well, that are all doing really well, I thought would want to have this service. service. So I had the idea and a significant part of the byside to package together to an airline to bring private flyers onto their mothership, which is the domestic part of their travel. But anyway, to answer your question. So things like that. Good ideas, lucrative, but for me at that

point in my life, to put, I feel, I don't know if I have the energy to do it. It's going to 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 I don't. I don't still have that. Well, 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 six months ago or something like that. And you were like, pickles. It's, yeah, you're 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 me and Ben started paying

attention. We're like, hey, what's Jesse? It's dealing with pickles. Well, okay, he's kind of right. Yeah. There's no brand and 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. 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 our running conversation. I'm starting to see at races, pickles at the, at the aid stations, they never existed 10 years ago. Pickle juice never existed 10 years ago at the eight stations of marathons and your local 5K.

To help you with running? Yeah. Yeah. So that made my intent. 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, you know, it's a big remedy for hangovers. But my point is, like, 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 was like, what the the hell is this? I just ran on. I'm going to so so I started doing so I started thinking about it and I'm like you know what I can't even name three pickle companies and I love pickles I don't even know free 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 can do it and he's going to be like that's the business plan well listen so I I I researched like the seven best tasting pickles and of the seven best tasting pickles I think it was like uh

the today's show did or something. It's like someone credible did it. I only knew one of the companies. So I'm like, if I only know one of this 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. So 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'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 Valsic or Vlasic? I like that company. But I think Mount Olives is the biggest ones.

I always get the little ones that look like a witch's toe. Are you wearing a metal out on a pickle shirt? I'm not. Look, I'm not, I'm not big. This is a big pickle. around with a clatterson pick. Won't just respect to that company. I don't even know.

But I'm just saying like, have you ever seen they were wearing the hat? Jesse, oh my God, 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, 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 do it with the Beast. That's right. That's right. Who needs Matt David? We got Jimmy now. Yeah, where's David?

I need to go get Ben, He seems like a good pickle guy. I need to know about Feast's low aggravation, though. I only want the low aggravation partners. I don't know about that one. Mount Olive does $220 million in revenue a year, privately owned. It sounds doable, man. Sounds like our money, right guys?

Yeah. Yeah. I want to thank that very much. For holding it for us. Yeah. Shoot a text over the 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. It's like, you come on here, you got to bring fresh ideas. You can't just only talk about your history. And you go, you tell me, you go, I got 50 ideas at my top drawer. I said, all right, say no more.

But you hit it at me. By the way, the pickle name sound like a rap name. Sweet Gherkin, bread and butter, kosher dill. Like, these are all rap names, man. Yeah. Yeah. We're about to have those little bit of those pickles. All right.

Tell me about this idea. You gave me three words. I don't know what the idea is, but you said, ready-made eight-ounce drinks. What's you got in mind? Yeah. So, I mean, I've been accumulating ideas in my top draw for 35 years. I love starting them, Sean, you know? But yeah, I mean, I don't mind.

By the way, if you guys want to rub— Anyone wants to run with this, you can. I'll think a one penny, royal deal. I'll give it to charity. You know, I think, like, I go back to five-hour energy. The brilliance of five-hour energy is they took a, you know, 12-ounce energy drink. They shrug it down at two and a half ounces, right?

That's what five-hour energy was. and why did it work? 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 it was like on the countertop at checkout impulse buy. They were selling 10 million two and a half ounce bottles every week. 10 million. When you look around retail at the counter at checkout at checkout, of retail, the countertop is incredibly crowded.

And you go to Whole Foods, there's gum, there's mince, there's this, there's that, there's chocolates, everywhere you go, gas stations, there's lottery tickets, and the, blah, blah, 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, the, the, the, felt stank, you know, the stands and the crowded space and all the Choshkes and stuff that you see at gas stations and at grocery and, and other retailers. And I think there's a tremendous opportunity.

I was going to call them quickies. To have like ready-made shots. Same thing as by about 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 going to be great goose vodka, but I see an opportunity. And if not that, someone should go make a deal and in a very fragmented, now you got me thinking, Sean. Now I'm not, this was here on my radar,

but here we go. Like the freestyling shit you were talking about, I was playing at. 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, Now, you go to your local liquor stores. Like the guy, my neighbor owns a liquor store. I go there and get the wine and this and that. Do a roll-up. Go pay someone for the, go rent the countertops of all the liquor stores. And then go to an abisco, 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. I love it. Yeah, 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 or better idea, the idea. 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 not. Not censor itself and wait until it has a fully form perfect idea, but actually just start to go and then know that I'm going to hop from this to this to this to this. There, that'll be the line. And that's all I need to do is get to that one that one line. I'm going to show you this too. This is, this is something I'm selling now. This is, I don't know, are we on, are we on. Are we on YouTube too? Are we on? No, or video, video, video, this is by 2024 all planned out. This is next year, fully, almost fully bait.

What my year looks like? My races. What's orange? There's a lot of orange on that. What does orange stand for? Orange. So when Sarah sold Spank, 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. We're going to Africa. We're going to New Zealand. But it's all mapped down. Yellow. What's yellow and what's green or blue, whatever that is? Yellow are my races and events. Green is my speaking.

Green is Oh, birthdays is this stuff Yeah 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 As Calender Club

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'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 two decades on you guys. And but I got I got the most experiential decades, I believe, on you guys.

You have the 40s and 50s, 30s, 40s, 50s. you know for me there's i'm in i'm in a coaching space you know um i speak a lot i have coaching programs the calendar but even the events that i do the running races and this kind of stuff 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 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 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 you just go do the liquor 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 of these are from today. All of these messages are for today. Pick one. Reddit. 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 going to 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 you sell a business is the same feeling you get when you finish 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 stole five of them. I have the right to say that. It's the same feeling. And 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 that's the reason, man. And so you're right. I had these businesses and, you know, there's no real plan around them. People like, what you would? I don't know. I'm just enjoying how it's making me feel right now.

And what's wrong with that? I got to scale just to scale because everyone told me out 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, in the markets. How's your portfolio set up? And what are you doing with your money? 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 dilittle it or sound in any way of obnoxious. And, 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 quite droople our money. Like we don't really think about it. It's like it spread out strategically and we live our life.

What's your monthly burn? I mean, what does one need to spend per month 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. Whatever that costs me, Sam, is what I'm going to spend on it.

How's that for an answer? Yes, Sam. I still want to ask you about something that you have talked about that I really liked, which is around your life philosophy. So you have a few of these that have made an impact on me. I don't know where I saw it. Some TikTok clip or something, you were talking about like this three-minute daily thing. You go three minutes, and I forgot exactly how you phrased it, but it was like, you go, I can network in three minutes, right?

I can invest in my friends, my network in just three minutes a day. And I'm always interested in anything that's like, you know, the six minute abs. I tend to be interested in the like, you know, shorter time frame type things. And you go compliments. What was the other ones? You go compliments. Complementing, congratulating, consoling. Explain that philosophy, because I've been doing.

that now where I basically go through my text list and I'm like, who's somebody I can compliment? Boom, send it out. And 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 like kind of like actually like a very effective little tip. I want you to share it with here. Well, in my 20s, I didn't have a way 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's a great way to get through the clutter of email, DM, social, you know, all this

stuff. 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 three minutes a day is, you know, I have sent a text, you mentioned the K Academy, Coach K. I sent a 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 have to respond. I just want to let you know. Like, it makes me feel like an eight-year-old for five days a year. I want to thank you 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, you might do nothing. But now if I see Coach Kay, I have permission to go over and say, coach, I send you a text. Like, I know if you got it, but like, I had that permission to do it. I'm not coming out of left field.

like, oh, hey, coach. You know, like, well, you just... So that took me 45 seconds to hit scent. Write it and hit sent. So I was like, okay, if I did three of those a day and just took three minutes and just started hitting friends, suppliers, manufacturers, inflip, whatever, over the course of a year,

I'll send a thousand. I'll plant a thousand permission slips all over the country and whirl. Three minutes a day. So in carpaline, 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 congratulating consoling is really just kind of three things that I like 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 going to pass away. Like, your life's going to 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, you can't, human nature, you can't even help but take inventory. Who reached out and who did? You're just aware. I just lost my father. I know everybody that called me.

I know everybody that did. 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 consult. The people that, you know, something happens to a friend in your life that's great. You want to congratulate them, you know? And then you want to compliment. You know, Sean, man, Sam, listen, you guys have been 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 want to congratulate you on your success, man. You know, you just call someone out of nowhere. You default to calls or texts?

Either way. I just think, I personally like handwritten letters. Here's one. 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 probably 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 them, you know, but you compliment, you graduate and consult and you do that to people. And like, if I, Sam, if I hit you up, God forbid you had something bad.

And I don't even know. I just met you for the first time. Other than the question about my burrow rate, I love you. So if I would pull you up after one meeting and say, Sam, man, I heard about XYZ. Man, I'm so sorry that happened to you. And then four months later, I'd call you up and say, Sam, man, you guys just hit five million downloads a day. Congratulations, man. And then I call you up again to the end of the end of the year.

I said, Sam, I just want to let you know, man, that question you asked me about my burn rate, you know, I would rethought it, and I want to 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 three things in that year. You're going to 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, well. Dad. Sean, 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. You know what? I build my career doing that. Well, so this is about relationships.

You also have others about skill building, life experiences. Explain some of your other kind of life rules because I think these are really worth sharing. 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 them at the end here. Because this is the stuff I've liked the most from your story. So talk about, you know, the sort of Misogi or 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 I really do two or three things every year. at the beginning of the year. This is actually perfect timing. I don't know when this is going to 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 seal, 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 them a Sogey, 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 should have something to show for it every year. By the way, if you're 35 years old, I don't 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 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 Cabot, which is every other weekend. I do something I normally wouldn't have done. Instead of watching 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 didn't know.

I coined it Kevin's rule because Kevin and I were camping at Mount Washington with our kids. And it was like, I go, Cadd, there's eight, it's like the winter, it's snowing, we're sleeping outside in a minus 40 sleeping bag, minus 20 sleeping bag. I'm like, Kev, there's eight billion people in the world, man. It's only us on this mountain. You know, 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 went to done. I'm like, well, what do you mean? He's like, so at the end of the year, I got six mini adventures. If you're 35 and you live to be 55 and you have six mini adventures, that's 300 mini adventures. and 30, 50, I'm sorry, 50 year defining things, you're Masogi, 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 many adventures that I've done

and by the way it only took six days of the 365 days of the year seven 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 got that's a great run that's a great run have you ever hung out with Rob Deere 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. 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 on them. 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 the.

this job that I actually don't like doing. And you're a great example. Your definition tends to be exciting and awesome because you do all these adventures, but it doesn't matter what your definition 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 incredible experiences and amazing relationships and moments, whether that moment took five seconds or, you know, five days or five 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, you know, trying to optimize every moment. in a generation of hustle and grind, which is so obvious, no shit.

You got to 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 you on very early on 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, yeah, my theory of life is find the people that you love and then do life

with them. And I just thought, oh, there's a North Star for me. Like, that's the new North Star. You know, maybe something, maybe something more wise will come take its place, but that's it. And that's the pot. I feel like I can rule the world. I know I could be what I want to. I put my all in it like no days off on a road. Let's travel. Never looking back.