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

1. 0:00 – 4:30

   Intro

   1. JIJesse Itzler0:00

      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 want 10,000 countertops. You wanna put your widget there?"

   2. SPShaan Puri0:14

      [laughs]

   3. JIJesse Itzler0:14

      "You wanna put your fucking widget there?" Keep the money warm, Shaan.

   4. SPShaan Puri0:18

      Yeah, keep the money warm for me. [laughs]

   5. JIJesse Itzler0:31

      [laughs]

   6. SPSam Parr0:32

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

   7. SPShaan Puri1:54

      Um, all right, well, welcome. We got Jesse Itzler here, um, also known as, I think you might be the richest runner, white rapper in the country. So congratulations, my friend.

   8. JIJesse Itzler2:05

      [laughs]

   9. SPShaan Puri2:07

      [laughs] We, uh, we, we are excited to have you here.

   10. JIJesse Itzler2:10

       I love that. If you keep adding categories, I could be the richest in the world, if you start adding, like, you know, that have four kids, that, um, uh, eat plant-based, et cetera, et cetera, so.

   11. SPShaan Puri2:20

       Right on. So, you know, I'm excited to talk to you 'cause you've done a bunch of amazing things. We've talked about you on the pod, and, uh, 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, uh, you reached out and said, "Hey, I'd love to come on." You have... I'm just gonna read a couple of these things. So I'm gonna flatter you real quick just so that the audience, uh, understands kinda just your background. So like we said, started out, uh, trying to make it as a rapper and ended up creating a, a, a jingles company. So you were making jingles for, for sports teams. Ended up selling that, then created, uh, Marquis Jets, a fractional jet owning company. Sold that to Berkshire Hathaway, which Warren Buffett obviously runs and owns. Uh, you're married to Sara Blakely, founder of SPANX. You are an epic sort of fitness athlete yourself, so a prolific runner. I read your book. Uh, the r- the day I got really into you was when I read Living with a Seal, which is the story of you living with, uh, David Goggins for 30 days. Um, I can't even really listen, like, David, David Goggins for 30 minutes on a podcast, uh, so living with him for 30 days, respect. And, um, yeah, you've created a bunch of companies out- outside of that partner with ZICO Coconut Water and, and doing a bunch of prolific things. So you have a, a very prolific c- career, but the start was, uh, like anybody. It was humble, humble beginnings. So talk about the early days when you were, you were trying to do the, the... Uh, let's start with the jingle company. You, um, you told me you were, you were sleeping on couches at the time trying to make it, and, uh, describe kinda what was going on at that time in your life. What was the plan and w- what were you going through and how did you come out of that?

   12. JIJesse Itzler3:57

       Well, I grew up in New York in the '80s when rap and hip-hop was starting to emerge in a bigger way, and that, it, that was the intersection of, of that happening and me going to college. So I was really into music early on. And while all of my friends in college were writing resumes and going on job interviews, I was like, "I'm making a rap record." Like, I, I'm... "Why would I waste my time making a resume? I wanna make an album."

   13. SPShaan Puri4:23

       [laughs]

   14. JIJesse Itzler4:24

       So it was like kinda that's the direction I wanted to go in, uh, right away. I ended up signing with a record company called

2. 4:30 – 7:30

   $10K for 10% of your life

   1. JIJesse Itzler4:30

      Delicious Vinyl. Everybody passed on me, and this one little record company gave me a shot, and I didn't have m- like, I wasn't super connected. I didn't have, like, a law- I, no, I did it all, I shopped it myself. But I ended up getting dropped from the label shortly after, and I got into writing, um, jingles or w- uh, for companies and theme songs for sports teams. And that was kind of my first entree into... You know, I pivoted. It, 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, um, yeah, that's how I kinda started out early on.

   2. SPShaan Puri5:08

      You told me you were sleeping on couches, um, trying to make it, and somebody offered you a tempting deal. They said-

   3. JIJesse Itzler5:17

      Yeah

   4. SPShaan Puri5:17

      ... "I'll give you $10,000 if I can get 10% of everything you'll ever make." H- how did that happen and w- what was your answer?

   5. JIJesse Itzler5:26

      Right. So I was, I was writing theme songs for sports teams. I was 22, 23 years old, and my business model was to write a song on spec and then cold call a professional sports team, try to get a meeting with them, try to, like, you know, get in there. And then if I was able to get that meeting, convince them that they needed a theme song, and that was my business model. And at the time I was, I was, I was bouncing around from couch to couch. I wasn't homeless, but my friends were. I'd just moved to New York from Los Angeles, and my friends were putting me up as I tried to figure out how to do it. I had no money to go in the studio to write any more songs on spec. So I needed money to fund that production. So a music manager said, you know, "I, I, I believe in you. I'll give you 10 grand for 10%, but I wanna own you for the rest of your life, basically 10% of anything you make." And I was like, "I'll take it," because-

   6. SPShaan Puri6:21

      [laughs]

   7. JIJesse Itzler6:21

      ... I needed the money to go to the stu- I thought it was the deal of the century.

   8. SPShaan Puri6:24

      [laughs]

   9. JIJesse Itzler6:24

      You're gonna give me 10 grand, and all I'm gonna do is pay you if I make it? Like, that sounded amazing to me.

   10. SPShaan Puri6:31

       [laughs]

   11. JIJesse Itzler6:32

       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 emer-" She asked me where I lived, and I said, "As of Monday, I have nowhere to live." I was getting kicked out of my friend's house on Monday. She said, "If it's an emergency, you can come live with my roommate and I." Monday, my friend kicked me out 'cause his parents were coming for a week, and I'm like, "This is an emergency."

   12. SPShaan Puri6:53

       [laughs]

   13. JIJesse Itzler6:54

       So I was living at Melissa's house, and I told her about this opportunity, and she said, "Well, why don't you go talk to my father before you give away 10% of your future earnings?" And as it turned out, her father was a very successful entrepreneur. He owned a company called Kinney Parking, parking garages in New York, and was, um, I think the second-largest shareholder of the New York Yankees.

   14. SPShaan Puri7:14

       You're like, "Melissa, your apartment is really nice." [laughs]

   15. JIJesse Itzler7:18

       What was amazing about that was it really wasn't, and that's why I really was taken aback by... I knew her dad was an entrepreneur. I didn't know the extent. And, um, sh- you know,

3. 7:30 – 13:30

   Can vs Will

   1. JIJesse Itzler7:30

      she sent me on... By the way, his name is Lou Katz. He passed away a couple years ago. He was an incredibly influential guy in my life, and this was my first encounter with him. So I went to, not to belabor this, but I went to see him, and it's, it's really relevant for anyone listening what he said to me as a 22-year-old. He- I told him my dilemma, "I'm gonna take 10 grand for 10% of my life," and he said to me, this is 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 m- I know I can..." And he, he took his notebook, and he literally threw it on the ground, and he said, "I didn't ask you that. I didn't ask you can you. I said will you."

   2. SPShaan Puri8:14

      Hmm.

   3. JIJesse Itzler8:15

      There's a big difference between can and will. I know you can start a podcast. I know you can be a millionaire. I know you can run a marathon. I, I said, "Will you, son?" And I said, "Yeah, wi- Lou, I will." He said, "Well, tell him to take the $10,000 and shove it up his ass."

   4. SPShaan Puri8:30

      [laughs]

   5. JIJesse Itzler8:30

      "Go make it work." And I did. You know, like, it was a really powerful lesson in, 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 wanna do. Let me go figure this out. And he, he breath- he blew that flame into me at an early age, and, um, it's really been a theme throughout my life in all the buckets of my life, the, the whole will vs. can notion. Y- you know?

   6. SPShaan Puri8:57

      And why, why is that so powerful, the will vs. can?

   7. JIJesse Itzler9:00

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

   8. SPShaan Puri10:00

      So you know what's really funny? Uh, after you told me that, so I did a call with you the other day to just prep for the, for the pod, say, "Hey, you know, uh, we're gonna talk about, I'm thinking about talking about this, this, and this. You have any good stories?" And you told me this, this will vs. can thing, and, uh, the next day [laughs] my wife was literally like, she's like, "Hey, can you take out the trash?" And I was like, "No, no, no, baby."

   9. JIJesse Itzler10:18

      [laughs]

   10. SPShaan Puri10:19

       "It's not about can I take out the trash."

   11. JIJesse Itzler10:21

       [laughs]

   12. SPShaan Puri10:22

       "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... 'Cause it's, once you see it, it's actually everywhere. Uh, Ben texted, Ben who's listening on this thing right now, he texted me this morning. He's like, um, he was like, "Hey, how'd you eat this weekend? We're, we're both, like, on a, a fitness kick." He's like, "Can you stay locked in from now till Thanksgiving?" And I just, I was like, "Oh, Ben, you asking me can? We're, we don't ask can questions anymore."

   13. JIJesse Itzler10:44

       Mm-mm.

   14. SPShaan Puri10:44

       As of meeting-

   15. JIJesse Itzler10:46

       Yeah

   16. SPShaan Puri10:46

       ... Jesse Itzler, I no longer ask can I. It's will I or won't I. That's it.

   17. JIJesse Itzler10:51

       Well, think about how many times in your life someone s- you, you, you say something that you've done, like, you know, "I did, you know, rim to rim." I, I'll take physical activities, or, "I climbed Kilimanjaro," and you explain to someone. They're like, "Oh, I c- I can do that." And I, you know, like, m- in the back of your head, you're like, "Yeah, you probably can, but, you know, will you do it?" You know?

   18. SPShaan Puri11:08

       [laughs]

   19. JIJesse Itzler11:08

       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.

   20. SPShaan Puri11:17

       By the way, Jesse, y- I have one other story that you, you don't know about. Uh, so you used to go to something, uh, at least you went once, called Coach K's Fantasy Camp. Is that correct?

   21. JIJesse Itzler11:28

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

   22. SPShaan Puri11:31

       Okay, e- okay, perfect.

   23. JIJesse Itzler11:32

       That's hilarious.

   24. SPShaan Puri11:32

       So you went to this thing. So for those who don't know, Coach K, he was the, the greatest college basketball coach at, at Duke. I went to Duke, and, um, my roommate, Trevor, used to volunteer at Coach K's Fantasy Camp, and volunteer was literally volunteering. I was like, "So what are you... You're staying over from break?" 'Cause it's, like, during some break, and he's like, "Yeah, I'm not going home. I'm gonna work this thing." I'm like, "Cool. How much you getting paid?" He, uh, he's like, "I don't think we really get paid, but, uh, you know..." Whatever. Like you just said, put himself in a position for something good to happen. And so he, and what I di- what he didn't know and what I didn't know was the only people who go to this camp that costs, like, 10 grand to go to are basically, like, business ballers trying to, like, live out their dream of, like, oh, as if I was an athlete. And he's, he- so he w- all he was doing was driving the shuttle back and forth between where y'all were staying and the thing, and he's like, "Dude, it's amazing." He's like, "Just hearing these conversations, what they're talking about in this, like, nine-minute shuttle ride..." He's like, he, 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, liked this guy, he loved this guy's energy." He goes, "And he tipped me 100 bucks for this, like, 10-minute shuttle ride." And he, later, I told him, he, I told him, uh, I was mentioning to him that you're coming on the pod. He goes, "That was the guy who tipped me." So I don't know if you remember this or not, but we took that tip, and, uh, we had a business idea at the time, and we needed to convince this, uh, famous chef in LA to come fly out and partner with us. We had no money. And so w- you, you plus w- a little, like, side job that I had became the money we paid for for the ticket to fly that guy out, which definitely changed the trajectory of our life. So little did you know.

   25. JIJesse Itzler13:11

       I, I love that. And, um, yeah, I've been going there for, since I'm 35. It's for guys 35 and older. And it's not to chase some, some crazy dream. It's a combination of, you know, um, meeting amazing people and also kinda, like, there's not a lot of times... I'm 55, so I'm, I'm older than you guys,

4. 13:30 – 17:30

   Going from Jingles to Jets

   1. JIJesse Itzler13:30

      and, um, I can't stop that clock, you know? Uh, uh, time's undefeated. It's always ticking. It's, 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.

   2. SPSam Parr13:49

      I don't know, man. I follow you on Instagram. It seems like you live like an eight-year-old a lot of times.

   3. SPShaan Puri13:52

      [laughs]

   4. SPSam Parr13:52

      I'm pretty sure I just-

   5. JIJesse Itzler13:53

      I got a lot, I got a lot... I do, I do, I do, I do.

   6. SPSam Parr13:54

      [laughs]

   7. JIJesse Itzler13:54

      I shouldn't say that.

   8. SPSam Parr13:55

      I'm pretty, I'm pretty sure I just saw you, like, in an RV with, like, eight friends just, like, running around the country.

   9. SPShaan Puri14:00

      Playing hacky sack. [laughs]

   10. SPSam Parr14:01

       It seems like you... Yeah, it seems like you got the eight-year-old life kinda nailed down.

   11. JIJesse Itzler14:05

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

   12. SPSam Parr14:11

       Yeah. I, I, I think, I think you've done that all right. You, uh... And then w- was your first, um, kinda major business Marquis Jet? So you went from, did you go from jingles to jets?

   13. JIJesse Itzler14:21

       Yeah, so interestingly, I had a... 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-

   14. SPShaan Puri14:32

       [laughs]

   15. JIJesse Itzler14:32

       ... um, I was doing jingles for like, uh, uh, honestly, like Turbo Bubble Gum, this, like, bubble book gum company that no one ever heard of, like, just anything that would pay me to-

   16. SPShaan Puri14:41

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

   17. JIJesse Itzler14:45

       I, 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 Knicks. I had done a, a commercial, a radio ad for a company called In the, In the Paint Clothing. It was owned by, um, uh, Nancy Grunfeld, Ernie Grunfeld, the GM of the Knicks' wife, and she really liked what we had, what I had done. And she said, um, "Yeah, if you have any other ideas, you know, let me know." I said, "Well, I'd love to do something for the Knicks. You know, like, write a theme song, and we can shoot a video. They can sing it in the arena." So I, I approached the Knicks to do this song called Go New York Go, and, um, the Knicks paid me $4,000 to buy the song outright. I'll never forget it. Like, um, I actually borrowed money to go in the studio to do this, to do the song. I didn't have enough money to go in the studio to record it, because they were paying me 30 or 60 days later, and by the time I paid the studio, the engineer, the lawyer that I had, the singer, the producer, it cost me $4,800 to actually deliver the song that they were paying me $4,000 for. And when I look back on it, you know, for most people, they would be like, "That's a terrible business model." It was the best business model in the world for me because when you start out, you know, people buy into stories, momentum, and people very often more than the products. Like, I was the business plan, and I would've paid the Knicks 10 grand to say they were my customer. Because once I had the Knicks, those phone calls to get onto the other sports teams became very easy, and that became my calling card. So I built a business around that, Shaan, that actually, I, I ended up doing theme songs for almost every professional sports team and turned it into a business where we were selling CDs. Like, the so- 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 bucks, and then we had, there was an earn-out 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.

   18. SPShaan Puri16:59

       [laughs]

   19. JIJesse Itzler17:00

       And I moved into my own space.

   20. SPSam Parr17:02

       What was your take-home after that?

   21. JIJesse Itzler17:03

       I had a partner, and at the end of the day, I think the, on the first 4 million, I made, like, a million and a half or... But by the way, a million and a half dollars to me-

   22. SPShaan Puri17:14

       All the money

   23. JIJesse Itzler17:15

       ... I was Elon Musk.

   24. SPShaan Puri17:16

       [laughs]

   25. JIJesse Itzler17:18

       Before Musk was born, I was walking around like I was Musk. I had a million and a half dollars. I would go to the, wake up at the eight and go to the ATM. I would get my, a printout of my balance.

5. 17:30 – 23:30

   Jesse’s underdog mentality

   1. JIJesse Itzler17:30

      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."

   2. SPSam Parr17:41

      It was like-

   3. JIJesse Itzler17:41

      "I'm going back to bed."

   4. SPSam Parr17:43

      [laughs]

   5. JIJesse Itzler17:44

      "See how I'm making more money in bed."

   6. SPSam Parr17:45

      [laughs]

   7. JIJesse Itzler17:47

      My partner convinced me to take all $1.3 million that we both cleared after taxes or whatever it was and reinvest it to s- to, to get, like, exclusive deals in all the s- like, we made the busi- we in- reinvested it in the business and actually made the business a lot bigger, and we got our earn-out. And then a- then everything changed a little bit for me. But, you know, I had no idea how to manage money. My parents never talked about money. My dad owned the plumbing supply house. Um, my mom raised four kids. The, the thing, the, our, I had no relationship with money. That might sound weird, but like people talk about relationships with, in terms of their relationship with their kids or their significant other, but not in terms of their relationship with time, which is very important, and your relationship with money, which is equally as important. I had no relationship with money. So when I got money, I didn't know how to save it, how to spend it, how to use it, how to act around it. I was very immature around new money. And you know what happened to me then? I lost it because I didn't know anything about it. And fortunately, I, I was able to bounce back through having other successful businesses and failures, but no one ever told me about it.

   8. SPShaan Puri19:07

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

   9. JIJesse Itzler19:11

      Overspending, thinking like, "Oh, that was pretty easy, man. I could just, I could do that again." You know, um-

   10. SPSam Parr19:16

       What did you buy?

   11. JIJesse Itzler19:18

       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.

   12. SPSam Parr19:30

       And that's pretty common, right? Like, you know, Shaan 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... Th- there's usually two types of people I've noticed, is people who have cashflow businesses or they're like a lawyer or something like that, or they own a law firm. Something where your, like, income is going up a nice amount every year, and you get used to having that cashflow. And then the other group of people are typically young folks who sell their company, and typically, those people are like me, where I paid myself $20,000 year 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."

   13. JIJesse Itzler20:11

       Yeah.

   14. SPSam Parr20:11

       And that's like a pretty, that's like a pretty common thing is... I, I don't think, I don't, I don't know if most people blow it, but I think it takes about two or three years to accumulate, uh, and, and kinda get used to and learn what to do. But there's no one to teach you.

   15. JIJesse Itzler20:22

       And the problem is I w- I'd always been taught, oh, if you're a mil- like, a millionaire was-

   16. SPSam Parr20:28

       That ain't shit

   17. JIJesse Itzler20:29

       ... w- 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."

   18. SPSam Parr20:35

       Right.

   19. JIJesse Itzler20:35

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

   20. SPSam Parr20:45

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

   21. JIJesse Itzler20:48

       Yeah, you go out and 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.

   22. SPShaan Puri20:58

       You, um... I, I'm a big believer that most of life, uh, most of your life kind of is a result of this, the conversation you have with yourself in your head. Do you remember after you kind of had that first hit, and you see the money, and you still have... You're only 27, you still got all your life ahead of you. Do you at all remember, like, the conversation you had with yourself? Like, "All right, Jesse, so, like, now X." And whether X was a good a- good, a good conversation with yourself or a misleading one, do you remember what, what the conversation you had with yourself at that point in time was?

   23. JIJesse Itzler21:28

       You know, it's interesting, 'cause Shaan, I was living in New York, and most of my friends were working on Wall Street. They were working at hedge funds. They were making, they were making a lot of money arou- 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 you- yourself. You can go down a, a, and spiral downward very quickly. And you know, what I was making, what it took me years to make and build and sell, and my journey to get to that point was crazy. I was selling carrot and cel- 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 st- I cleaned meat trucks. That didn't work. I sold chicken, shrimp, and meat door to door. That didn't work. I mean, a jingle company. D- I, it went on and on. So, you know, I had really worked so hard and, and at the same time, like, I'd invested so much, not for the money, but just, like, I just wanted to get a record deal, man. I didn't care about the money. I just want... Everyone said, "You can't do it." Everybody. And it was, it was such a driver. If I remember, I listened to a podcast where one of you guys w- with Laird Hamilton, and you were saying how that a- he was saying how that, you know, you, one of you guys were saying you need that anger to inspire you. Like, you need some kind of fuel, you know? So, um, I had that. I still have that. Don't get me wrong. I still have that, and I, I'm, I never wanna lose that underdog mentality. I never wanna be like, "I'm at the top of the mountain." I, I'm not. I consider myself back of the pack everything. Back of the pack sales, back of the pack entrepreneur. There's so many better entrepreneurs than me, um, so many better salesmen than me. But I, I, but I love that feeling of I gotta prove myself. So when it, the money happened, it was just like, oh, Steve Stark is making so much more than me. We're in the same basketball run. Like, I gotta catch Stark.

   24. SPSam Parr23:28

       [laughs]

   25. JIJesse Itzler23:29

       Y- you know?

6. 23:30 – 32:30

   Marquis Jet: The craziest origin story of all time

   1. SPSam Parr23:30

      The, um, the Marquis Jet thing, that's interesting though, 'cause that's, like, totally out of left field, so... A- and that seems like a, a, a way bigger win than the jingle business.

   2. SPShaan Puri23:39

      And the s- same partner, right? Same, same co-founder?

   3. JIJesse Itzler23:41

      Yeah, same partner. Um, it was a much bigger win, and it w- like most things in my life, um, they... Most of the businesses that have, that I've been involved with weren't planned, you know? And most of my successes in life haven't been in my business plan. They've been opportunities that presented themself. You know, my whole life I've been taught when opportunity knocks, you know? And I'm not, I don't wanna sit around waiting for opportunity to knock. I like to create my own o- uh, my own opportunity. And I was a guest on a private jet with my partner, and I was like, "You, people fly... Like, what is this?"

   4. SPShaan Puri24:20

      [laughs]

   5. JIJesse Itzler24:21

      "What is this that I'm on?" And we, 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, be in a fractional program like NetJets, but even that is a really big commitment, both in capital and time. It's a five-year commitment, lot of money up front. That wasn't... I mean, that wasn't an option for us. Or you could charter, and there were a lot of questions around, well, who owns the plane? Who are the pilots? You know, do I feel comfortable on that? What if the plane doesn't show up? So we found a little white space there and said, "You know what? We only wanna fly, like, 25 hours a year, and I bet there's a lot of people like us that don't wanna own an airplane, don't want the responsibility, but they just wanna be able to have the, um, have a plane available on short notice." And that was the idea around selling a 25-hour jet card that work, work, like, work like a debit card. So if, if you and, if you and Sam, Shaan, 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 in my life, many times it's been through partnership. We partnered with N- NetJets. They ended up buying us to use their airplanes. Partnered with Coca-Cola at ZICO, at ZICO coconut water. They ended up buying us. Um, so, but anyway, that was, that's what happened. We were a guest on the plane and, you know, walking around, eyes wide open looking for opportunities and said, "Wow, this could be really interesting." And, uh, and then started the journey of figuring out how we could pull this off, because we had no aviation experience, very little money, and, you know, I was younger than you guys. I was 28, 29 years old, and, um, figuring out, like, man, we need a lot of airplanes.

   6. SPShaan Puri26:18

      [laughs]

   7. JIJesse Itzler26:18

      Where do we go for airplanes? And, uh, and then started that journey of, of building this company.

   8. SPShaan Puri26:24

      So you walk in, you walk into NetJets and you're like, "Hey, uh, I'm Jesse, former rapper, jingle-preneur."

   9. JIJesse Itzler26:31

      [laughs]

   10. SPShaan Puri26:31

       "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?

   11. JIJesse Itzler26:41

       Well, at first we didn't. They kicked us out of the office-

   12. SPShaan Puri26:43

       [laughs]

   13. JIJesse Itzler26:44

       ... in the first meeting after about 12 minutes.

   14. SPShaan Puri26:46

       [laughs]

   15. JIJesse Itzler26:47

       And, um, 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 1000 on their SATs into a room to pitch them the idea? A year before that, I was a yes guy my whole life. I, I, I was, I, I've, I've kind of, and I still try to pride myself when people ask me for things to deliver if I can, but never ask for anything in return. You know? Like, I'm not like, "Oh, Sam. I'll do this for you, Shaan, but, like, can you do this for m-" Like, I don't op- 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.

   16. SPShaan Puri27:31

       [laughs]

   17. JIJesse Itzler27:33

       This guy was having a, his daughter was having a sweet 16, and Chris, um, a famous singer was performing in his hometown. His daughter wanted to bring her sweet 16 to the event. The guy says, "I know you know the manager. Can you hel- help this guy get some tickets and do anything special?" Turns out, I get the, the guy's daughter as a backup singer for one song with the mic off.

   18. SPShaan Puri27:54

       [laughs]

   19. JIJesse Itzler27:55

       Everyone at school the next day is... She's, like, the hero of this. Like, "What happened? Oh my God." They're freaking out. The guy calls me up, he goes, "I don't know who you are. I don't know what you have, what you do. But you lit my daughter up, and if you ever need anything, let me know." Like, turns out, he w- I can't make this up. He's the president of NetJets a year later.

   20. SPShaan Puri28:15

       [laughs]

   21. JIJesse Itzler28:16

       I need 650 airplanes.

   22. SPShaan Puri28:18

       [laughs]

   23. JIJesse Itzler28:18

       I call him up like, "Jim, you're never gonna believe this. The, the guy who got your daughter on, I have an idea for a thing." He gets me the meeting. We get thrown out of the meeting 12 minutes in because they're like, "We're not giving two kids access to our 650 airplanes." And this guy, Jim Jacobs, comes up to me after the meeting and goes, "You know what? That was amazing." I said, "We got thrown out in 12 minutes. What do you mean amazing?" He goes, "Rich Santulli, my partner, he doesn't give anyone 12 minutes." He goes, "This is something. Come back next week and bring this thing to life. Re-pitch it. I need more information." So we came back the next week and we realized we could never sell them in a PowerPoint, which was, like, what every guy sees 100 PowerPoints every year. We brought in our own focus group. We had eight people in the lobby.

   24. SPShaan Puri29:00

       Mm.

   25. JIJesse Itzler29:00

       And they walked in one by one, and they stood up and said that they would never buy a fraction of an airplane, what NetJets was selling, but they would buy a 25-hour jet card. And at the end of the meeting, they literally said, "If you guys raise money or put up your own money, if you can figure it out, we'll give you a shot." And a y- a couple years later, we had more customers than NetJets.

   26. SPShaan Puri29:20

       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 i- 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.

   27. JIJesse Itzler29:39

       When I think back on this moment at 28 years old, and we had, like, Carl Banks from the New York Giants. I think Run from Run-DMC was there. It was right behind me on the wall. Um, you know, and these guys-

   28. SPShaan Puri29:49

       At that meeting?

   29. JIJesse Itzler29:50

       Yeah. We brought, we brought him in. We brought him in. And when we said when, when, when we, they got up one by one and explained why this card would work, and, you know, I think what they realized was they had been pitching to a, a much older corporate client, and that they, what they realized, I think, in the meeting was, here are these two 27-year-old kids. And by the way, remember I said people buy into people's stories and momentum? This had nothing to do with our product. The decision-maker looked us in the eye and said, "I see enthusiasm. I see someone that's, no matter what, even they have, though they have no aviation experience, is gonna make this work, and I'm willing to bet on these two guys." It wasn't, there was no PowerPoint. It was us. Like you're the business plan. You are the business plan. So at the end of the meeting, he literally said to us, w- after we got the deal and, you know, like year one we did a, I think we did like close to 200 million in sales year one. And I remember going into his office and, and asking, I said, "Rich Santulli," who is like, he knighted me, man. He knighted me. I said, "Rich, w- how did we, how did 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, Kenny and I, my partner and I, that he wanted to bet on. And, you know, I just wanna say this for, for anyone listening here, because I know this is primarily a business podcast. By the way, it took me 37 minutes to warm up, but now I'm fully here.

   30. SPSam Parr31:54

       [laughs]
7. 32:30 – 38:30

   How Marquis Jets worked

   1. JIJesse Itzler32:30

      And, um, you have to bring that meeting to life. You have to stand out. You have to, you know, not in a gimmicky way, but you have to make that memorable, man. And, and fortunately, we were able to do that. And, and it worked. And then we had an amazing f- amazingly fruitful relationship and partnership with NetJets until we exited.

   2. SPSpeaker32:52

      [upbeat music] Our software is the worst. Have you heard of HubSpot? See, most CRMs are a cobbled-together mess, but HubSpot is easy to adopt and actually looks gorgeous. I think I love our new CRM. Our software is the best. HubSpot. Grow better.

   3. SPSam Parr33:11

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

   4. JIJesse Itzler34:57

      I can only run marathons. I can't run any business. [laughs] I'm not good at running anything. No, I'm a terrible operator. I'm a terrible manager. But I'm really good at knowing that I'm terrible at that and being okay with it. So, you know, we were able to hire a CEO right away. Um, 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 ins- before Instagram. I'm not so good at the In- uh, now with Instagram, but back when there was no Instagram, I was good at creating PR-able opportunities and, and talk-worthy events. And, um, for my era, that was really important. So no, um, 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.

   5. SPSam Parr35:46

      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 ch- made money off the, uh, a membership?

   6. JIJesse Itzler35:54

      No. So we, the original deal with NetJets was we were leasing time on their planes, but I wouldn't have to, we wouldn't have to enter into a long-term lease until we sold it, so we had no risk. They were carrying all the paper. So if I bought, if you and, if Sam, Shaan, 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, we have a f- 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- You know, 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. Um, it was a true, um, no lose for both parties.

   7. SPShaan Puri36:49

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

   8. JIJesse Itzler36:57

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

   9. SPShaan Puri37:00

      This was before Berkshire owned it. Is that right?

   10. JIJesse Itzler37:03

       NetJets sold it to Berkshire prior to us.

   11. SPShaan Puri37:06

       Okay.

   12. JIJesse Itzler37:06

       And then, and then we went to, now we're part of Net- now Marquis Jet's now part of NetJets.

   13. SPShaan Puri37:10

       Did you get just-

   14. JIJesse Itzler37:11

       Which is our gold member

   15. SPShaan Puri37:11

       ... did you get Berkshire stock? 'Cause that would've been a good stock to just get in the deal.

   16. JIJesse Itzler37:15

       I know, right?

   17. SPShaan Puri37:16

       Right?

   18. JIJesse Itzler37:16

       No, we didn't.

   19. SPSam Parr37:17

       NetJets sold for 725, 725 million in '98. Um, and half of it was paid in stock, so that was, um, if, if, that was a good deal for NetJets depending on-

   20. JIJesse Itzler37:28

       If they-

   21. SPSam Parr37:28

       I don't know what the revenue was, but that, that's a lot of money.

   22. SPShaan Puri37:31

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

   23. SPSam Parr37:38

       200.

   24. SPShaan Puri37:39

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

   25. JIJesse Itzler37:43

       No, it is. The av- no, 'cause our, our average, our average customer spent close, I think it was 250 or $235,000 a year.

   26. SPShaan Puri37:52

       Gotcha. Okay.

   27. JIJesse Itzler37:52

       So-

   28. SPShaan Puri37:52

       But, and it's more like a GMV, so, 'cause you have to... So your take is some spread between that and then whatever NetJets... Okay, gotcha. So-

   29. SPSam Parr38:00

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

   30. JIJesse Itzler38:06

       Well, this is 30 years ago.
8. 38:30 – 43:00

   Getting celebrities as first customers

   1. SPShaan Puri38:30

      y- you're like, "I'm on this plane." I'm like, "Holy shit. This is an amazing way to fly. I'd love to do this. I'm sure other people would love to do this." You come up with the idea. Cool. Now how do you go get those first people to give you $200,000 to be a part of this, right? That's like a, a huge, like... Where did you go find those customers and, and tell the story of kinda how you got it off the ground.

   2. JIJesse Itzler38:52

      Well, we were start, we started out, you know, I think the first thing that any entrepre- most entrepreneurs, at least in our position in, at Marquis Jet, is we had to establish credibility. 'Cause if I was gonna sell you time on a plane, and you said, "Who flies with, who flies with you guys?" That would be my first question, or one of them. And I said, "Oh, my dad and my next-door neighbor," you probably would leave. But if I was like, you know, Oprah, Bill Clinton, you'd be like, "Wow, they must have vetted this," you know? So we started out looking for athletes, entertainers, and, and high-profile people, um, which was not easy for me. Um, but I had to go where wealthy people congregated, and I heard about this, you know, they could afford time on a jet. I heard about a conference in Monterey, California, that was just getting some traction called TED.

   3. SPShaan Puri39:36

      Yeah.

   4. JIJesse Itzler39:36

      So I flew out to Monterey, and um, you know, I told the guys, like, "Hey, I'm gonna go get my first sale."

   5. SPShaan Puri39:42

      [laughs]

   6. JIJesse Itzler39:42

      "I'm going to this thing called a TED Talk." They were like, "What?" You know?

   7. SPShaan Puri39:47

      [laughs]

   8. SPSam Parr39:47

      Who's TED?

   9. JIJesse Itzler39:47

      And it, it's in Monterey, California. You gotta like, you can't even get there.

   10. SPShaan Puri39:51

       [laughs]

   11. JIJesse Itzler39:51

       You have to, like... I connected through Chicago into whatever, rented a car, five hours to Monterey. I get to the TED. It's like Fort Knox, man.

   12. SPShaan Puri39:59

       Yeah.

   13. JIJesse Itzler40:00

       Everybody has a credential. Like, this, like huge, and I'm like, "You need a credential to get in here?" There's no credentials to be found. So I'm thinking, like, "How am I gonna sneak in, buy someone's pass, like, go into the room where all the qualified leads are?" I'm in this coffee shop plotting, like, you know, my, my, my entrance or how I'm gonna do it, and every two hours a wave of people come in and they're buying. They have these credentials, and I'm like, "Oh, this is where they come on their break." And they're all buying lattes and muffins, and these lattes and muffins and whatever. Lattes and muffins. So the next morning I got up at 5:00, and I bought all the muffins from this-

   14. SPShaan Puri40:35

       [laughs]

   15. JIJesse Itzler40:35

       I controlled all the muffin inventory in Monterey, California. And I literally just waited and... This is a true story, by the way. And it's, it's been verified. You can walk... So two hours later, this guy, uh, the first wave of people on the break walk in, and the guy orders a latte and a muffin. I stop him. Uh, they tell him that, that they can give him a latte, but they're all out of muffins. It's like fucking 9:00 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?"

   16. SPShaan Puri41:14

       [laughs]

   17. JIJesse Itzler41:15

       And, um, I started talking to him, and he's like, you know, "What are you here, I'm here for the conference." I'm like, "Me too. What do you do?" I tell him what I do. He said, "You gotta be kidding me. I'm in the market for a private jet card." And his name was Josh Kopelman. He owned a company called half.com.

   18. SPSam Parr41:28

       Famous VC, right?

   19. JIJesse Itzler41:29

       Oh, is it me?

   20. SPSam Parr41:29

       Now he is.

   21. JIJesse Itzler41:30

       I bumped into him, like three years ago at, uh, at a retreat and, and we were, we were talking about this. And anyway, he was my first sale.

   22. SPShaan Puri41:38

       [laughs]

   23. JIJesse Itzler41:39

       He was my first sale. And, 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 verse can, of putting myself in a situ- situation where I could attract that kind of luck. Y- you know? And, and, um, he was my first sale though, Shaan, to answer your question. And, and you know what happened after that? I'm gonna tell you what happened after that. I serviced the hell out of him. I did what everybody listening would do, but I did 30% more. So when he went to Mexico, he expected me to return his call and d- every DM, DM and all that. Of course, I did what everyone here would do. But he went to Mexico, he didn't expect the list of pediatricians that I vetted in case his kids got sick.

   24. SPShaan Puri42:28

       Mm.

   25. JIJesse Itzler42:28

       He didn't expect me to make reservations every Wednesday at, at, every night at 8:00 during spring break in Mexico in case he and his wife wanted to go to dinner. And, and, and after a couple of months of doing that, what he didn't expect me to do He gave me the magic word. He gave me a referral. And that was rinse and repeat for, for five years until we grew this. So no, I was never the CEO. I was never the, the, the operator. I was never the COO. I was, I wasn't even...

9. 43:00 – 54:00

   Zico: Finding profitable super niches

   1. JIJesse Itzler43:00

      I don't even think I was on the org chart. [laughs]

   2. SPSam Parr43:02

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

   3. JIJesse Itzler43:29

      And the tequila company with The Rock, yes.

   4. SPSam Parr43:32

      You've done a good job of hiring.

   5. JIJesse Itzler43:34

      No, we were the Boston Celtics, man.

   6. SPSam Parr43:36

      [laughs]

   7. JIJesse Itzler43:37

      We, we were the Boston Celtics. We, from, like, the old... We, we, the talent at this company was exceptional. Ken Austin is an exceptionally... I don't, he could be the m- he is such a talented guy, and, um, I learned so much from Ken. And, you know, we had great sales reps, and we attracted really good talent because we built a really good culture.

   8. SPSam Parr44:06

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

   9. JIJesse Itzler44:16

      Definitely.

   10. SPSam Parr44:17

       Just so happens-

   11. JIJesse Itzler44:17

       Definitely

   12. SPSam Parr44:17

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

   13. JIJesse Itzler44:25

       It w- it w- 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, uh, s- uh, it was something, some-

   14. SPShaan Puri44:41

       Including, uh, Garrett Camp, the guy from Uber. He created, he tried to do an Uber for jets, uh, that didn't work out, right?

   15. JIJesse Itzler44:48

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

   16. SPShaan Puri44:57

       The other business you did a partnership on was ZICO Coconut Water. And, uh-

   17. JIJesse Itzler45:01

       Yeah

   18. SPShaan Puri45:01

       ... I think this is interesting 'cause now we're seeing a pattern. The first is you're picking businesses in, like, categories that they're not in the MBA curriculum. Nobody's thinking about, oh, sports teams need slogans and CDs that'll 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. M- nobody's even looking in that area at the time, right? There'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 nonexistent, really, at the time. Um, and I think ZICO was pretty small when you found it. It's not like it had, like, you know, tons of momentum. Um, so talk about two things. Number one, finding these niches. Like, what, what is it that, 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 wanna hear the full version of it.

   19. JIJesse Itzler46:00

       [laughs] Oh, with ZICO?

   20. SPShaan Puri46:03

       Yeah.

   21. JIJesse Itzler46:04

       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. W- tried to figure out. This is w- there were no, there was no coconut water in the stores at the time. This is, I'm a... So let me back it u- up even further. I was running a 100-mile race, and I did a lot of tr- when I was doing my training, I did a lot of research around hydration and nutrition. If I'm gonna run for arguably 24 hours, how many calories do I need to eat a, drink an hour? Um, how many calories do I need to take in an hour? How much fluid ounces do I need to drink an hour? How much salt do I need an hour? And my research led me to coconut water. So I ran this race powered by coconut water, and I finished it in 22 hours and 30 minutes. When I was done, I'm like, "This is gonna be, this is the new Gatorade. No one knows about this. I'm the human guinea pig. I'm bringing this to market." Y- you know? It's a better option. It's all natural. One ingredient. You know, it rains, God sends it up a tree, we crack it open, and we drink it. Like, this is... I mean, are you kidding me? So I spent a year trying to figure it out, how to import it, and I realized, like, I did get a 980 on my SAT, 'cause I couldn't figure it out. But I knew I could market and sell it. I knew I could. So again, same model, same formula. I took it, the idea, to Coca-Cola. The president of Coke's Emerging Brands division, um, was friends with one of my customers at Marquis Jet. He got me a meeting. I pitched the meeting. Uh, I, in the meeting, I pitched this idea of coconut water. He takes a liking to me, but he says, "We don't buy PowerPoints. We're Coca-Cola. We buy brands." [laughs] He goes, "But if you partner with another company or something, you know, maybe we can, that, uh, that, that's out there that has proved that they can make the product, ship the product, get it in stores or whatever, we'll come in and we'll partner with you." So I went to ZICO, and that's how we formed the partnership. During the meeting, the, um, a- about a week before, I was at, um, Matt Damon's house, and Matt was also a customer of Marquis Jet, and I did the things that I did for Josh Kopelman with Matt, and we became friends. And I said to Matt, you know, he'd asked me if I wanted to spend the night, they were going out, and I said, "I'm going to Brazil in a day or two. I can't stay." 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."

   22. SPShaan Puri48:40

       [laughs]

   23. JIJesse Itzler48:42

       He's like, "I drink coconuts." He goes, "If anything happens f- w- you know, with this company, let me know. I may wanna get involved." A month later in the meeting at Coke, like the meeting is going so bad, I'm showing this PowerPoint, you know, like, a- and, and out of nowhere, like I know I had to change the whole-

   24. SPShaan Puri49:00

       Energy

   25. JIJesse Itzler49:00

       ... feel of the meeting.

   26. SPShaan Puri49:01

       Yeah.

   27. JIJesse Itzler49:01

       I just turned to the president, the guy at Coke, and I'm like, "You know, my partner Matt Damon and I."

   28. SPShaan Puri49:05

       [laughs]

   29. JIJesse Itzler49:06

       And the guy went, "Matt Damon's your partner?"

   30. SPShaan Puri49:09

       [laughs]
10. 54:00 – 56:20

    Business Idea 1: Private travel experience for commercial travelers

    1. JIJesse Itzler54:00

       no, I don't even know today what it is. But I could spend $50,000 on a private flight, which is amazing, or I could buy a first class ticket for 1,500 bucks. 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 i- 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-

    2. SPShaan Puri54:35

       That, that's smart. It's like you, like, unbundled the private experience. It's like, okay, there's the jet part of it.

    3. JIJesse Itzler54:40

       Yeah.

    4. SPShaan Puri54:40

       But then there's the-

    5. JIJesse Itzler54:41

       Right

    6. SPShaan Puri54:41

       ... walk onto the plane-

    7. JIJesse Itzler54:43

       Yeah

    8. SPShaan Puri54:43

       ... walk off the plane.

    9. JIJesse Itzler54:43

       Once you get, like, like, 'cause when, once you get on an airplane, do you really care?

    10. SPSam Parr54:47

        Doesn't-

    11. JIJesse Itzler54:47

        I mean, it's-

    12. SPSam Parr54:47

        Yeah, it doesn't matter.

    13. JIJesse Itzler54:48

        I'm in 1A. No one's bothering me in 1A. I don't-

    14. SPSam Parr54:51

        And in some regard, the commercial jet is safer.

    15. JIJesse Itzler54:53

        Yeah.

    16. SPSam Parr54:53

        You have more amenities. So yeah, like I, but I've been on a- I flew first class, uh, from New York to LA one time for, like, some meeting. I w- I had never flown first class, but I did it because I, it ha- it was overnight and I had to be ready for a meeting. And I get on, I was 1A, and 1B, or sitting right next to me, was Stephen A. Smith.

    17. JIJesse Itzler55:10

        [laughs]

    18. SPSam Parr55:10

        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-

    19. JIJesse Itzler55:16

        Right

    20. SPSam Parr55:16

        ... I guess if you're famous. Uh-

    21. JIJesse Itzler55:18

        Right

    22. SPSam Parr55:18

        ... what, what is that?

    23. JIJesse Itzler55:20

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

    24. SPShaan Puri56:19

        Well, you,

11. 56:20 – 1:00:00

    Business Idea 2: Pickles!

    1. SPShaan Puri56:20

       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, [laughs] and you were like, "Uh, guys, pickles." And, you know, it seemed like, you know, the guy who was saying coconut water when nobody was talking about coconut water, he's talking about pickles. So me and, me and Ben started paying attention. We're like, "Hey, what's Jesse Itzler doing with pickles? Well, okay, he's kinda right."

    2. JIJesse Itzler56:44

       Yeah.

    3. SPShaan Puri56:44

       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-

    4. JIJesse Itzler56:52

       Yeah

    5. SPShaan Puri56:52

       ... present and future. Um, what do you see in the pickle market?

    6. JIJesse Itzler56:55

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

    7. SPShaan Puri57:19

       Does it help you with running?

    8. JIJesse Itzler57:19

       And now they're popping up. Yeah, so that made my antennas stick-

    9. SPSam Parr57:22

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

    10. JIJesse Itzler57:29

        Oh, yeah, in Russia, it's a, it's a, you know, it's a big remedy for hangovers. But my point is, like, it ma- it put my antennas up. Like, what is this? Y- you know? Just like when I saw the first thing of coconut water on a shelf, I was like, "What the hell is this?" I just ran 100, I'm gonna... So, so I started doing, so I started thinking about it. And I'm like, you know what? I can't even name three pickle companies. And I, I love pickles. I don't even know-

    11. SPShaan Puri57:55

        [laughs]

    12. JIJesse Itzler57:55

        ... people for free.

    13. SPShaan Puri57:56

        This is, by the way, this is the part-

    14. JIJesse Itzler57:57

        So that's when-

    15. SPShaan Puri57:57

        ... where he's gonna bring in a focus group of 10 people, and he's gonna say-

    16. SPSam Parr58:00

        [laughs] Yeah

    17. SPShaan Puri58:00

        ... "Name a pickle company," and nobody can do it, and he's gonna be like, "That's the business plan."

    18. JIJesse Itzler58:04

        Well, listen. So like, I, I researched, like, the seven best-tasting pickles. And of the seven best-tasting pickles, I think it was, like, uh, the Today Show did or something, you know, it's like, it's like, someone credible did it. Um, I only knew one com- 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 it, it, that's where it started, and I'm like, "This is a category with no innovation, no fun." You know, 75% of Americans eat pickles. The average American eats, like, 10 pounds a year. That's more than cereal. And I'm like, "I like it here."

    19. SPSam Parr58:51

        [laughs]

    20. JIJesse Itzler58:51

        "I like this space."

    21. SPSam Parr58:53

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

    22. SPShaan Puri58:55

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

    23. SPSam Parr58:57

        I like Claussen. I like Mount Olive. Is it called, uh, Vlasic or Vla- Vlasic? I, 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. I've-

    24. JIJesse Itzler59:08

        You ever worn a Mount Olive pickle shirt? Are you-

    25. SPSam Parr59:11

        I'm not. Look.

    26. JIJesse Itzler59:12

        Are you wearing-

    27. SPSam Parr59:12

        I'm not the-

    28. JIJesse Itzler59:12

        I'm just saying, I-

    29. SPSam Parr59:13

        I'm not big-

    30. JIJesse Itzler59:13

        I imagine you-
12. 1:00:00 – 1:02:00

    Business Idea 3: Quickies-Ready-made 8oz Drinks

    1. SPShaan Puri1:00:00

       [laughs]

    2. JIJesse Itzler1:00:00

       Yeah.

    3. SPSam Parr1:00:01

       Yeah. [laughs]

    4. JIJesse Itzler1:00:02

       I wanna thank them very much.

    5. SPShaan Puri1:00:03

       For holding it for us.

    6. JIJesse Itzler1:00:05

       Yeah, for holding... [laughs]

    7. SPSam Parr1:00:07

       [laughs]

    8. JIJesse Itzler1:00:07

       Yeah, can you do that? Shoot a text over to the CEO of Olive and just let him know to keep that money warm for us, all right? [laughs]

    9. SPSam Parr1:00:13

       [laughs]

    10. SPShaan Puri1:00:13

        We'll be there soon. Um, you, what other ideas you got? 'Cause I, I, I told you, I was saying, you know, uh, you'll get this 'cause, you know, you're a, you're, 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. It's like, "Okay, if you come on here, you gotta freestyle." And we're trying to do that of the business realm, where it's like, you come out here, you gotta bring fresh ideas. You can't just only talk about your history. And you go, you tell me, you go, "I got 50 ideas in my top drawer." [laughs] I said, "All right, say no more." But you hinted at me.

    11. SPSam Parr1:00:43

        By the way, uh, the, the, the pickle names sound like a rap name. Sweet Gherkin.

    12. SPShaan Puri1:00:48

        [laughs]

    13. SPSam Parr1:00:48

        Bread and Butter. Kosher Dill. Like, this, these are all rap names, man. [laughs]

    14. JIJesse Itzler1:00:52

        Yeah.

    15. SPShaan Puri1:00:53

        Yeah.

    16. JIJesse Itzler1:00:53

        Yeah.

    17. SPShaan Puri1:00:54

        We're about to have-

    18. JIJesse Itzler1:00:54

        That's hilarious

    19. SPShaan Puri1:00:55

        ... Migos Pickles. Um, all right.

    20. SPSam Parr1:00:57

        [laughs]

    21. SPShaan Puri1:00:57

        Tell me, tell me about this idea. You, you gave me three words. I don't know what the idea is, but you said ready-made 8oz drinks. What, what you got in mind?

    22. JIJesse Itzler1:01:05

        Yeah. So I mean, I, I've been accumulating ideas in my, in my top drawer for 35 years. Um, I love starting things, Shaan, you know, but, um, yeah, that, I mean, and I, I don't mind. By the way, if you guys wanna run, anyone wants to run with this, you can. I'll take a one penny-

    23. SPShaan Puri1:01:23

        [laughs]

    24. JIJesse Itzler1:01:24

        ... royalty and I'll give it to charity. Um, you know, I think, like I go back to 5-hour ENERGY. The brilliance of 5-hour ENERGY is they took a, you know, 12-ounce, uh, energy drink, they shrunk it down to two and a half ounces, right? That's what 5-hour ENERGY was. And why did it work? They, they only, I believe, I believe they only at 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 at... It was like on the countertop at checkout, impulse buy.

13. 1:02:00 – 1:08:00

    Jesse Itzler's Philosophy on Money

    1. JIJesse Itzler1:02:01

       They were selling 10 million two and a half bottle- ounce bottles every week. 10 million. When I look a- 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 da da da da da. The only place that I've found, like where there's open area, are liquor stores. If you go into a liquor store, you don't see the, the, the, the, the self stand, you know, the stands and the crowded space and all the tchotchkes and stuff that you see at gas stations and at, at grocery and, and, and other retailers. And, um, I think there's a, a tremendous opportunity, I was gonna call 'em Quickies, um, to have like ready-made shots, same thing as, as 5-hour, like of your Woo-Woo, Lemon Drop, whatever your favorite, Kamikaze, ready-made drinks are, right at the countertop, that are already made, fresh ingredients, you know, where people could just come and grab and go and have a ready-made cocktail that they could bring to tailgates, parties, et cetera. I'm not saying it's gonna, it's gonna be Grey Goose Vodka, but I see an opportunity. And if not that, someone should go make a deal in, in, in a very fragmented... Okay, now you got me thinking, Shaan. Now I'm like, this wasn't even on my radar, but here we go.

    2. SPShaan Puri1:03:24

       [laughs]

    3. JIJesse Itzler1:03:25

       Like the freestyling shit-

    4. SPShaan Puri1:03:26

       Exactly

    5. JIJesse Itzler1:03:26

       ... you were talking about on 20/20. Um, really even a better idea would be to go it... Liquor stores are, that is the most fragmented market out there. They're all mom and pops. There's no like chain of liquor st- I mean, da, like, you know, 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 the, 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 want 10,000 countertops. You wanna put your widget there?"

    6. SPShaan Puri1:04:04

       [laughs]

    7. JIJesse Itzler1:04:05

       "You wanna put your fucking widget there? Keep the money warm, Shaan."

    8. SPShaan Puri1:04:09

       Yeah, keep the money warm, baby. [laughs]

    9. JIJesse Itzler1:04:15

       [laughs]

    10. SPShaan Puri1:04:15

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

    11. JIJesse Itzler1:04:18

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

    12. SPShaan Puri1:04:31

        Right. Yeah, yeah, exactly. Exactly, and it, uh, you, you're kinda like, I think the background of rap... I'm not, I'm not joking about this. I, I think the, the way the brain can sort of like-

    13. JIJesse Itzler1:04:41

        It's-

    14. SPShaan Puri1:04:41

        ... not censor itself and wait till it has a fully formed perfect idea, but actually just start to go and then know that, oh, I'm gonna hop from this to this to this to this, and there.

    15. JIJesse Itzler1:04:50

        Yeah.

    16. SPShaan Puri1:04:50

        That'll be the line, and that's all I need to do is get to that one, that one line.

    17. JIJesse Itzler1:04:54

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

    18. SPShaan Puri1:04:59

        I saw this.

    19. SPSam Parr1:05:00

        This is on YouTube too.

    20. JIJesse Itzler1:05:00

        Are we on, yeah, on here or are we-

    21. SPSam Parr1:05:02

        No, video, video, video

    22. JIJesse Itzler1:05:03

        ... on Google? This is my 2024 all planned out. This is next year, fully, almost fully date what my year looks like, my races, my, um-

    23. SPShaan Puri1:05:13

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

    24. JIJesse Itzler1:05:16

        Orange, orange are, are, so when Sara sold Spanx she wanted to do a lot of traveling, so this year we committed as a family to go on the road. So all the orange, as crazy as this looks, is all travel.

    25. SPShaan Puri1:05:28

        Oh, wow.

    26. JIJesse Itzler1:05:29

        We're going to Africa, we're going to New Zealand, but it's all mapped out.

    27. SPShaan Puri1:05:32

        Yellow, what's yellow-

    28. JIJesse Itzler1:05:33

        See, orange-

    29. SPShaan Puri1:05:33

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

    30. JIJesse Itzler1:05:36

        Yellow are my races and events. Green is my speaking. Uh, green is, oh, birthdays and stuff. Yeah.
14. 1:08:00 – 1:18:00

    Jesse Itzler's Philosophy on Relationships: Compliment, Congratulate, and Console

    1. JIJesse Itzler1:08:00

       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 Marquis Jet? Work 20-hour days? I mean, like, that's not gonna give me that sense of impact, legacy for my kids, um, and just the feeling, quite honestly, that I have. I mean, like, it's indescribable. A wire's a wire. You get the wire and it's like the same feeling you get when, when you sell a business is the same feeling you get when you finish the mara- a marathon, you walk an old lady across the street, or you do anything that makes you feel good about yourself. I swear to God. And I have the right to say that 'cause I sold five of them. I have the right to say that. It's the same feeling, and for the, for, for very, very, for a lot of people, chasing that, waiting 20 years to sell a business or something to have that feeling, when I feel like I get that every single day. And that's a really powerful place to be in your life at 55. And, and that's the reason, man. And, and so you're right. I had these businesses and, you know, there's no real plan around them. People are like, "What's your...?" I don't, I don't know. I'm just enjoying how it's making me feel right now. And what's wrong with that? I gotta scale just to scale because everyone told me I had to scale? I don't wanna do that, man.

    2. SPSam Parr1:09:29

       Right.

    3. JIJesse Itzler1:09:29

       I did that.

    4. SPSam Parr1:09:30

       So a question that we like to ask people is, it's a really simple question, but we, 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, I don't like the Elon Musk path of, uh, all these sacrifices and, uh, um, 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, I, I, I'm, I'm a former college athlete runner, so I, I like watching what you're doing. Um, 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, um, and um, when you're financing, uh, this, are you just, are you using your speaking fees to finance it and then you have your Marquis Jet money in just one big account in the, in the markets? H- how's your portfolio set up and what do you do with your money?

    5. JIJesse Itzler1:10:19

       Well, just, you know, it's, um... I don't know, man. Like, we, we, we never really think about it that much. I know that's, I don't wanna 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. Um, we're not trying to triple it or quadruple our money. Like, we don't really think about it. It's like it's spread out strategically, and we live our life.

    6. SPSam Parr1:10:48

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

    7. JIJesse Itzler1:10:54

       I like to ride my bike. I like to run. I like to swim. I like to speak in public. I like to be around my family and friends. What- whatever that costs me, Sam, is what I'm gonna spend on it. How's that for an answer?

    8. SPSam Parr1:11:12

       [laughs] Yes, Sam. [laughs]

    9. JIJesse Itzler1:11:14

       I still love you, Sam. Um-

    10. SPShaan Puri1:11:17

        Well, I wanna 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 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 compl- you go, "I, I, I can network in three minutes," right? I, uh, I can, I can invest in my friends, my fi- 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, I tend to be interested in-

    11. SPSam Parr1:11:52

        [laughs]

    12. SPShaan Puri1:11:52

        ... the, like, you know, shorter timeframe type things. And you go, "Compliments..." What was the other ones? You go compliments, um-

    13. JIJesse Itzler1:11:59

        Complimenting, congratulating, consoling

    14. SPShaan Puri1:12:00

        ... consoling. E- explain that, that philosophy, 'cause I've been doing that now where I, I basically go through my text list and I'm like, who's somebody I can compliment? Boom. Send it out. And they love it, 'cause they're like, uh, you know, I'm thinking of them. We haven't talked in a little while. It's really simple for me to do. This is, like, kind of like a, a, actually like a very effective little tip I want you to share with here.

    15. JIJesse Itzler1:12:21

        Well, in my 20s I didn't have a way to, to... I had no, I was really on a super tight budget. I was writing 10 handwritten letters, I mean, a year. Not every single day, but pretty much. Writing about 10 handwritten letters a day, and that was my entire marketing strategy. And I realized that, you know, it, it's a great way to get through the cl- the clutter of email, DMs, soc- you know, all this stuff. 'Cause a lot of people don't check their emails, or their assistant does or whatever, but everyone reads a handwritten letter. So I, the three minutes a day is, you know, I had sent a text, you mentioned the K Academy, Coach K. I sent a, uh, flew into Carolina, um, not too long ago, and I sent Coach a, a text thanking him for having the event. And I said, "You don't have to respond. I just wanna let you know, like, it makes me feel like an eight-year-old for five days a year and I wanna thank you for, for doing this. I know you don't have to do it." And it took, and like I realize like he might share that with his team, like we're having an impact. Like, look at, look at this note. Or tell his wife. He might do nothing. But now, if I see Coach K, I have permission to go over to him and say, "Coach, I sent you a text, like I don't know if you got it." But like I have that permission to do it. I'm not coming out of left field like, "Oh, hey coach." You know, like, whoa, you just... So that took me 45 seconds to hit send. Write it and hit send. So I was like, okay, if I did three of those a day, and just took three minutes, and just started hitting friends, suppliers, manufacturers, influ- whatever, over the course of a year, I'll send 1,000. I will plant 1,000 permission slips all over the country and world, three minutes a day. So in carpool line when I take my kids to school or pick 'em up, I just fire off a couple of emails or call 'em or whatever. So that was that theory. The compliment, congratulate, and consoling is really just kind of three things that I, I like to, to remind myself to do to maintain and build authentic relationships. Authentic relationships, not relationships. Authentic relationships. So for example, if you have somebody in your life that's grieving, and you don't reach out to them, and you guys are young, but you'll see in the next 10 years friends will start to get diagnosed with stuff, parents, grandparents are gonna pass away. Like your life's gonna change, man. If you have someone that's grieving and you don't reach out to them, they will never forget it. They'll nev- oh, th- th- th- it, you can't, human nature, you can't even help but take inventory who reached out and who didn't. You're just aware. I just lost my father. I know everybody that called me. I know everybody that didn't call me. And the people that didn't call me don't get a pass. They don't get a pass. So you always wanna console. The people that y- you know, something happens to a friend in your life that's great, you wanna congratulate 'em, you know? And then you wanna compliment. You know, Shaan, man, Sam, listen. You guys have an, a amazing podcast. You did it yourself. You know, you guys decided to like build some businesses, and here you are, you know, bringing on inspiring people to inspire entrepreneurs all over the world. And, um, I just wanna congratulate o- you on your success, man. I'm, you know, I, you just call someone out of nowhere and-

    16. SPShaan Puri1:15:44

        You default to calls or texts?

    17. JIJesse Itzler1:15:46

        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.

    18. SPShaan Puri1:16:07

        Mm-hmm.

    19. JIJesse Itzler1:16:07

        But you know, so if I was 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 closeout the year process that I kinda teach people, but like, and that's one of them. Y- you know? But you compliment, you congratulate, and console. And you do that to people, and like if I, Sam, if I hit you up, God forbid you had something bad, and, and, and I don't even know, I just met you for the first time. Other than the question about my burn rate, I love you.

    20. SPShaan Puri1:16:41

        [laughs]

    21. JIJesse Itzler1:16:44

        So if I, if I were to-

    22. SPShaan Puri1:16:46

        Love you

    23. JIJesse Itzler1:16:46

        ... call you up after one meeting and say, "Sam, man, I heard about X, Y, Z. Man, I'm so sorry that happened to you." And then four months later I call you up and say, "Sam, man, you guys just hit five million downloads a day. Congratulations, man." And then I call you up again at the end of the year and I say, "Sam, I just wanna let you know, man, that question you asked me about, about my burn rate, you know, I re- rethought it, and I wanna compliment you because you asked the tough questions. And you know what? That's the seat that you're in, and I give you credit for asking questions like that to people on the other end, and I really admire you for that." I do those three things in that year, you're gonna think differently about me.

    24. SPShaan Puri1:17:23

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

    25. JIJesse Itzler1:17:30

        All right. Well, well-

    26. SPShaan Puri1:17:31

        Dad

    27. JIJesse Itzler1:17:31

        ... well, come on. Come on. Come on. Shaan, 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?

    28. SPShaan Puri1:17:41

        You're right.

    29. JIJesse Itzler1:17:42

        Who doesn't want to be a hero? We, like if you're telling me I, I don't have to run into a building and save, save someone, I can just do that and I can be a h- quote-unquote hero, like you know what? I'd build my career doing that.

    30. SPShaan Puri1:17:54

        Well, so this is about relationships. You also have others about skill building, life experiences. Explain some of your

15. 1:18:00 – 1:23:51

    Jesse Itzler's Philosophy on Defining a Year

    1. SPShaan Puri1:18:00

       other kinda life rules, 'cause I think these are really worth sharing. Uh, you know, people I think will be entertained and inspired by the business stories, but my hope is that that actually was just buying the right to drop a little wisdom on 'em at the end here, 'cause this is the stuff I've liked the most from y- from your story. Um, so, so tell, talk about, you know, the sort of Misogi or the, the Kevin's Rule. Like these are pretty foundational.

    2. JIJesse Itzler1:18:24

       Yeah, well, that goes into kind of the planning that I showed you on the calendar, and um, I really, I do, do two or three things every year, um, at the beginning of the year. This is actually perfect timing. I don't know when this is gonna air, but like November, December, when you look into 2024 or the next year, I try to have one big year-defining thing on my calendar every year. Last year was my bike ride across America. 2015 was Living with a Seal, the book I wrote. 2017 I lived at a monastery. 2016 or something I started 29029, this company with my partner. So there's an old Japanese ritual called the Misogi, and we took the liberty to kind of create our own version of what that means. But basically, it means that every year you do one, or the way I've interpreted it, is you do one big year-defining thing. And you h- you should have something to show for it every year. By the way, if you're 35 years old, I don't wanna, I don't, just rounding up here, um, and you live to be 85 So you have, that would be 50 year defining things between now and the end of your, and the end of your run that you have on your life resume. That's pretty damn incredible. The second thing I do is something I call Kevin's Rule, named after my friend Kevin. Um, which is every other weekend, I do something I normally wouldn't have done. Like, instead of watching like a George, the Georgia football game, I might take my kids fishing. I might go to a conference. I might, you know, um, watch some, spend a couple of hours learning something I, I didn't know. Um, I coined it Kevin's Rule because Kevin and I were camping at Mount Washington with our kids, and it was like, I go, " Kev, there's 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, it, how often do you do this?" 'Cause he invited me. He's like, "Oh, every other week." He's a police officer. "I do, so every other month I do something I normally wouldn't have done." 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, your Misogi, and 300 mini adventures. Shaan, 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 death bed, and you're like, "Jesse, man, thank you. I took your advice listening to my podcast, and I now have 50 unbelievable adventures. I've done the Grand Canyon. I've taken my family here, and I have 300 mini adventures that I've done. And by the way, it only took six days of the 365 days of the year, seven days of the 365 days of the year." If they're 2%, is that 2%? 6%? What is that?

    3. SPShaan Puri1:21:16

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

    4. JIJesse Itzler1:21:19

       Okay, there we go. [laughs] That's a great run. That's a great run.

    5. SPSam Parr1:21:25

       Have you ever hung out with Rob Dyrdek? You, you guys are really similar. We had him on, um, and I, I think I've said publicly he's one of my favorite people. Uh, and you have a 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.

    6. SPShaan Puri1:21:40

       You, you live life on your terms, which is what, like 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.

    7. SPSam Parr1:21:50

       Because even successful people don't do that.

    8. SPShaan Puri1:21:52

       Yeah.

    9. SPSam Parr1:21:52

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

    10. SPShaan Puri1:22:13

        Well, o- 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 f- you know, five days or f- five weeks, it doesn't really matter. It's like maximizing, kinda like th- squeezing the juice out of, out of the fruit, you know? Versus, versus, uh, you know, trying to optimize every moment.

    11. JIJesse Itzler1:22:50

        I- in a, in a, in a generation of hustle and grind, which is so obvious, no shit, you gotta work hard. That message gets lost. And you don't wanna 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.

    12. SPShaan Puri1:23:12

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

    13. SPSam Parr1:23:33

        And, uh, that's the pod. [upbeat music]

Episode duration: 1:23:56