Jesse Itzler's Exact Playbook For Creating HIT AFTER HIT

31:14And 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, young mogul, et cetera. They wanted that because that's incredibly valuable to get that person on their plane at a young age. but at the end of the day they he saw something in my penny and i my partner and i that he wanted to bet on and you know i just want to say this for 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 i'm fully here he's here i'm slow i'm slow today but i got it now um you know like i said that was never in our business plan.

32:06Oh, 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 at 27, walking in there and saying to my partner, like, this is as big as it gets, because you know what? There is no one else that has 650 airplanes. This is it. And you have to bring that meeting to life. You have to stand out. You have to, you know, not in a gimmicky way, but you have to make that memorable, man.

32:44And 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 good at running anything. No, I'm a terrible operator.

33:18I'm a terrible manager, but I'm really good at knowing that I'm terrible at that and being okay with it. So, you know, we were able to hire a CEO right away. which allowed me to focus on sales, which I was better at. Buzz, which I was really good before Instagram. I'm not so good now with Instagram, but back when there was no Instagram, I was good at creating PR-able opportunities and talk-worthy events. And for my era, that was really important. So no, 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?

34:02Is 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 the original deal with NetJets was we were leasing time on their planes, but 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, we have 4 ,000 members. We're doing a billion dollars a year.

34:44Then 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 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, and then we went to – now we're part of NetJets.

35:25Now T-Jets, now part of NetJets. Did you get 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 million in 98. And half of it was paid in stock. So that was a good deal for NetJets, 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 can't be membership dues. That would be insane. No, it is.

35:59No, because our average customer spent close, I think it was$250 ,000 or$235 ,000 a year. Gotcha. Okay. And it's more like a GMV. So your take is some spread between that and then whatever. Okay, gotcha. So yeah, I guess 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 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 uh 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 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.

36:52You 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 at Marquiset 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.

37:28But if I was like, Oprah, Bill Clinton, you'd be like, wow, they must have vetted this. So we started out looking for athletes, entertainers, and high profile people, which was not easy for me. But I had to go where wealthy people congregated. And I heard about this, 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 go out to Monterey and, um, you know, I told the guys like, Hey, I'm going to go get my first sale. I'm going to the thing called a Ted talk. They were like, what? It's in Monterey, California. You got to like, you can't even get there.

38:07You have to like, I connected through Chicago into whatever, rented a car, five hours in Monterey. I get to the Ted. It's like Fort Knox, man. And 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 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 going to do it. And every two hours, a weave of people come in and they're buying, they have these credentials.

38:39I'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 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, the first wave of people on the break walk in and the guy orders a latte and a muffin. I stop him. they tell him that they could give him a latte but they're all out of muffins it's like fucking nine in the morning he's like you're out of muffins the guy starts walking i stop him like sorry i overheard you i actually have an extra muffin if you want a muffin and uh 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 he's like you know what do you hear me 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 cart.

39:39And his name was Josh Koppelman. He owned a company called Half.com. Famous VC, right? Oh, he's amazing. Now he is. I bumped into him 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 can, of putting myself in a situation where I could attract that kind of luck. And he was my first sale, though, Sean, to answer your question. And you know what happened after that?

40:22I'm going to tell you what happened after that. I serviced the hell out of him. I did what everybody listening would do, but I did 30 % more. So when he went to Mexico, he expected me to return his call and every EM, DM, and all that. Of course, I did what everyone here 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 eight o 'clock during spring break in Mexico in case he and his wife wanted to go to dinner. And after a couple of months of doing that, what he didn't expect me to do, he gave me the magic word.

41:00He gave me a referral. And that was rinse and repeat for five years until we grew this. So no, I was never the CEO. I was never the operator. I was never the COO. I don't even think I was on the org chart. So 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 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 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 conor 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 We, the talent at this company was exceptional.

42:05Ken Austin is an exceptionally, he could be the, he is 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. Like, oh, you're here at this jet company. So I know like you're of someone. I know you're someone interesting. Just so happens. I work here or I own the company. I mean, it's like, it's a pretty wonderful experience, I imagine, to work at a private jet company.

42:40It 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 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 NetJets as a partner, I'm sure it wouldn't have worked as well. So a lot of things lined up for us. The other business you did a partnership on was Zico Coconut Water.

43:16And 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? 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.

43:52And 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 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 Zeke up? Yeah. Yeah. I spent a year trying to figure out how to have my own coconut water company. I went to Brazil. I went to Jamaica. Look, try to figure out this is, there were no, there was no coconut water in the store side.

44:32This is, I'm a, so let me back it up even further. I was running a hundred 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 going to run for arguably 24 hours, how many calories do I need to 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 the new Gatorade.

45:09No one knows about this. I'm the human guinea pig. I'm bringing this to market. It's a better option. It's all natural, one ingredient. 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 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 the idea to Coca-Cola. The president of Coke's emerging brands division was friends with one of my customers at Marquee Jack.

45:53He 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, maybe we can, that's out there, that has proved that they can make the product, ship the product, get it in stores or whatever, 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 marquee jet. And I did the things that I did for Josh Koppelman with Matt.

46:39And 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 me. He's like, I love coconut. I have a coconut tree in my backyard. He's like, I drink. He goes, if anything happens with this company, let me know. I may want to get involved. A month later in the meeting at Coke, the meeting is going so bad. I'm showing him this PowerPoint. And out of nowhere, I know I had to change the whole feel of the meeting.

47:17I just turned to the president, the guy at Coke, and I'm like, you know, my partner, Matt Damon, and I. and the guy's like Matt Damon's 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 Matt I need a favor he's like I'm like can I come over with a 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 alright 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.

48:01And we got the deal. And the creep, 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 me, making yourself stand out and be memorable in a meeting. Now I stretched it a little bit, 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.

48:37You, that's wild. By the way, Coke bought it two years later, a hundred percent. 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 regoes 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 your advantage?

49:15Well, 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 exited five businesses, but I've been able to build a family, keep my health, be a really good son to my parents. I have great friends. So I really I'm not, and I'm not using Elon as an example. 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'm really proud of the life that I built. So I really don't, I really say no to most.

49:59I 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. Come on, friend reduction, man. I want a low aggravation. You're doing layoffs? You're doing Zoom calls with people? Let them know, hey, I'm sorry, we had to make a reduction in friendship. We're doing layoffs. Excuse me, Mr. Damon, can you step out 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.

50:34That's great. It's so fun. Hey, quick message here, because you know that feeling when you send a wire and it actually works? No friction? Well, I've used Mercury for years now, and let me tell you, it just works. And that's why I use it for not one, not two, but eight of my companies. From credit cards to invoices, I have everything in one place. There's no janky dashboard. I'm never told, please visit a local bank branch. None of that tomfoolery. And a few months ago, I landed a big client. And the first thing I did, I sent them a clean, branded invoice. Boom. Deal closed. Cash in the door. That's the kind of banking experience I want.

51:07And that's why I use Mercury. So if you're running a startup and you want banking that feels like it's built in this century well go to mercury.com and get started in minutes mercury is a financial technology company not a bank bank the services are provided through choice financial group column a and evolve bank and trust members fdic but i'm not trying to you know push you really it's like it's based on my enthusiasm for something um how's it going to impact my life meaning like day to day um And 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.

51:46And 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 Marquee Jet. Like Marquee Jet was the biggest thing I'd done, you know. and I walked her through it and she goes, that's an incredible idea. Don't do it. What was it? I wanted to take, 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 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.

52:37So 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 on 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. bucks. 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 more. I don't even know today what it is. But I could spend$50 ,000 on a private flight, which is amazing. Or I could buy a first class ticket for$1 ,500. 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 you feel like okay because what you did 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 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 steven a smith and i was like how the fuck did 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.

54:21What 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 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 all doing really well, I thought would want to 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.

55:02But anyway, to answer your question, so things like that, good ideas, lucrative, but for me at that point in my life, I don't know if I have the energy to do this. 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 have, I don't, I don't still have that. Well, you, you, but you can't turn that switch off. Right. Cause 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 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.

55:42So me and me and Ben started paying attention. and we're like, hey, what's Jesse Itzel 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. 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 aid stations, they never existed 10 years ago.

56:16Pickle juice never existed 10 years ago at the aid stations of marathons and your local 5K. To help you with running? 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 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'm like, what the hell is this? I just ran 100. So I started thinking about it. And I'm like, you know what? I can't even name three pickle companies.

56:56And I love pickles. I don't even know. By the way, this is the part where he's going to bring in a focus group of 10 people. And 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 researched like the seven best tasting pickles. And of the seven best tasting pickles, I think it was like the Today 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.

57:34and 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 Clausen, like the big brand? Is that right? I like Clausen. 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 Mount Olive pickle shirt? I'm not.

58:15Look, I'm not. I'm not big. This is a big pickle. I've never seen you walking around with a Clatterson pickle. We'll disrespect to that company. I don't even know. But I'm just saying, have you ever seen anyone wearing a hat? Jesse, 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. And we're bringing our influencers into this market. I believe you on this opportunity. Why do that? Let's just get the Beast on the phone. Let's party with the Beast. Beast Pickles. That's right. That's right. Who needs Matt Damon?

58:44We got Jimmy now. Yeah, where's David? 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. Yeah, I don't know about that one. Matt Olive does$220 million in revenue a year, privately owned. It sounds doable, man. It sounds like our money. Right, guys? Yeah. Yeah. I want to thank them very much. For holding it for us. Yeah.

59:11Shoot a text over to 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 was saying, you'll get this because you're a rap guy. When you go on certain shows like The Breakfast Club or Sway in the morning, there's like an expectation. He's 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 in my top drawer.

59:44I said, all right, say no more. But you hinted at me. By the way, the pickle names 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 Nigos Pickles. um all right tell me 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 you got in mind yeah so I mean I I've been accumulating ideas in my in my top draw for 35 years um I love starting thems Sean you know but um yeah I mean I don't I don't mind by the way if you guys want to run anyone wants to run with this you can i'll take a one penny royalty i'll give it to charity um no i think like i go back to five hour energy the brilliance of five hour energy is they took a you know 12 ounce uh energy drink they shrugged it down to two and a half ounces right that's what five hour energy was and why did it work they they only i believe i believe they only have predominantly sold stores that would put it on the countertop when they started out.

1:00:56So 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 bottle ounce 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 blah, blah, blah. The only place that I've found where there's open area are liquor stores. If you go into a liquor store, you don't see the stands and the crowded space and all the tchotchkes and stuff that you see at gas stations and at grocery and other retailers.

1:01:47And I think there's a tremendous opportunity. I was going to call them quickies to have like ready-made shots. Same thing as five, 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 can bring to tailgates, parties, et cetera. I'm not saying it's going to, it's going to be great goose vodka, but I see an opportunity. And if not that, someone should go make a deal in a very fragmented, now you got me thinking, Sean.

1:02:26Now I'm not, this is what you're on my radar, but here we go. Like the freestyling shit you were talking about I was pointing 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, you go to 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.

1:03:06You want to put your widget there? You want to put your fucking widget there? Keep the money warm, Sean. Yeah, keep the money warm.

1:03:18oh 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 exactly and uh you're kind of like i think the background of rap i'm not i'm not joking about this 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 i'm gonna hop from this to this to this to this and there yeah 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 are we on are we on youtube YouTube too.

1:04:04Are we on all year? No, or video, video, video. This is by 2024, all planned out. This is next year, almost fully date, 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 of - 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 traveling. Oh, wow. We're going to Africa. We're going to New Zealand. But it's all mapped out. Yellow. What's yellow and what's green or blue, whatever that is? Yellow are my races and events.

1:04:42Green is my speaking. Green is, oh, birthdays and 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 Ice Cannon. 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.

1:05:24How old are you guys? How old are you, Sam? 34. I'm 35. So I got two decades on you guys. Um, and, but I got, I got the most experiential decades, I believe on you guys, the forties and fifties, thirties, forties, fifties. Um, 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 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.

1:06:22I'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. Read it. I said, I can't, and it was like, you changed my life or this has really inspired me or I did this or I saw my parents. I haven't seen my parents in a long time.

1:06:58And I talk about the importance of that very often, 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, 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, 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.

1:07:49I swear to God, and I have the right to say that because I sold 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 have these businesses and, you know, there's no real plan around them. People like, what's your, 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 I had to scale.

1:08:31I 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 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?

1:09:09And when you're financing this, are you just using your speaking fees to finance it? And then you have your marquee jet money and 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, I don't know, man. Like we never really think about it that much. I know that's, I don't want to belittle it or sound in any way obnoxious. In fact, I'm incredibly grateful, but like it goes back to the relationship with money from the beginning of the conversation. We're not trying to triple it or quadruple our money. Like we don't really think about it.

1:09:46It's like it's 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

1:10:20i want to ask you about something that you have talked about that i really liked which is uh around your life philosophy so you have a few of these that have made an impact on me you um i don't know where i saw 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 phrase it but it was like you go i can network in three minutes right i i can i can invest in my friends my fight my network in in just three minutes a day and i'm always interested in anything that's like you know the six minute abs i i 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 um complimenting congratulating consoling explain that 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 could compliment?

1:11:10Boom, 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.

1:11:48Because 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 fluid 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 grabbing an impact.

1:12:23Like, 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 out of left field. Like, oh, hey coach. You know, like, well, you just, so that took me 45 seconds to hit send, write it and hit send. 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, influx, whatever, over the course of a year, I'll send a thousand.

1:12:59I will plant a thousand permission slips all over the country and world three minutes a day. So in carpool line, when I take my kids to school or pick them up, I just fire off a couple of emails or call them or whatever. So that was that theory. The compliment 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.

1:13:43parents, grandparents are going to pass away. 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... 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 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 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 um i just want to congratulate you on your success man i'm not you know i 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 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 by like like in the pecking order, but you don't have the ability to do that.

1:15:15It 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.

1:15:47So if I would 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 four months later, I'd call you up and say, Sam, man, you guys just hit 5 million downloads a day. Congratulations, man. And then I'd call you up again at the end of the year and say, Sam, I just want to let you know, man, And that question you asked me about my burn rate, you know, I really thought it. And I want to compliment you because you ask 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.

1:16:21And I really admire you for that. I do those three things in that year. You're going to think differently about me. Oh, you'll be his hero. You'll be all of our heroes, to be honest with you. That'd be incredible. All right. Dad? Come on. Come on. 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? If you're telling me I don't have to run into a building and save someone, I can just do that and I can be a quote unquote hero. You know what? I built my career doing that. Well, so this is about relationships.

1:16:59You 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 you from your story. So so tell 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.

1:17:30And 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 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 the Misogi. And we took the liberty to kind of create our own version of what that means.

1:18:07But 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 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 Kevin, which is every other weekend, I do something I normally wouldn't have done. Like, instead of watching like a Georgia, the Georgia football game, I might take my kids fishing.

1:18:50I 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 in Mount Washington with our kids. And it was like, I go, Kev, 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 8 billion people in the world, man. It's only us on this mountain. And, 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 would have done.

1:19:21I'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 a misogy, 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.

1:20:05And 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 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 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 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.

1:21:02And you're a great example. Your definition tends to be exciting and awesome because you're doing all these adventures, but it doesn't matter what your definition of 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 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 versus uh you know trying to optimize every moment.

1:21:53In 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 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 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 uh that's the pod

1:22:41I feel like I can rule the world. I know I could be what I want to. I put my all in it like my days off. On the road, less travel, never looking back.

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