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

to go rent the countertops of all the liquor stores

and then go to Nabisco, one of the big boys,

and be like, hey, guess what?

I own 10,000 countertops.

You want to put your widget there?

You want to put your fucking widget there?

Keep the money one, Sean.

Yeah, keep the money one for me.

Yeah.

No.

No.

No.

No.

No.

No.

No.

No.

No.

No.

I want to put my all in it like the days off.

Okay, everyone, what's going on?

This is Sam.

We have Jesse Itzler on the pod today,

very fascinating guy.

He started a bunch of different companies.

The biggest one being 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.

We went deep into some of the numbers

behind some of his businesses.

We learned about his early career

and there's like a ton of takeaways.

The pod was only supposed to be 60 minutes long,

but Sean and I were like so into it that we went over.

I think we went like 90 minutes, something like that,

because his story is super fascinating.

If you liked the Rob Dierdek episode,

which a lot of people did,

I think our most listened to episode of all time,

I think you're really gonna like this one.

That was pretty spectacular.

I love feeling good about it.

And if you're watching this on YouTube, do me a favor,

hit that subscribe button and make a comment

because we've had a ton of people comment

on our videos lately and a ton of people subscribe.

We see the data behind it.

So it's awesome that you guys are doing this

and it means a ton of us.

We actually text each other all the time

when someone makes a funny comment.

So let us know.

And if you're listening on iTunes or Spotify,

hit that download or the subscribe button,

whatever it is on those platforms

because we get notifications about those 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.

All right, well, welcome.

We got Jesse Itzler here, also known as,

I think you might be the richest runner,

white rapper in the country.

So congratulations, my friend.

No, no, no.

We are excited to have you here.

I love that.

If you keep adding categories,

I could be the richest in the world.

If you start adding like, you know,

then have four kids that eat plant-based, et cetera, et cetera.

So right on.

So, you know, I'm excited to talk to you

because you've done a bunch of amazing things.

We've talked about you on the pod

and we sort of spoke it into existence.

I think we talked about it.

Somebody might have sent you a clip.

I'm not sure.

But you reached out and said, hey, I'd love to come on.

You have, I'm just gonna read a couple of these things.

So I'm gonna flatter you real quick

just so that the audience understands

kind of just your background.

So like we said, started out trying to make it as a rapper

and ended up creating a Jingles company.

So you were making Jingles for sports teams,

ended up selling that and created Markey Jets,

a fractional jet-owning company,

sold that to Berkshire Hathaway,

which Warren Buffett obviously runs and owns.

You're married to Sarah Blakely, founder of Spanx.

You are an epic sort of fitness athlete yourself.

So prolific runner.

I read your book, the day I got really into you

is when I read Living with a Seal,

which is the story of you living with David Goggins

for 30 days.

I can't even really listen.

I gave David Goggins for 30 minutes on a podcast.

So living with it for 30 days, respect.

And yeah, you've created a bunch of companies

outside of that partner with Zico Coconut Water

and doing a bunch of prolific things.

So you have a very prolific career,

but the start was like anybody.

It was humble beginnings.

So talk about the early days when you were,

you were trying to do the,

let's start with the Jingle company.

You told me you were sleeping on couches at the time,

trying to make it and describe kind of

what was going on at that time.

And you're like, what was the plan

and what were you going through?

How did you come out of that?

Well, I grew up in New York in the 80s

when rap and hip hop was starting to emerge in a bigger way.

And that was the intersection of that happening

and me going to college.

So I was really into music early on.

And while all of my friends in college

were writing resumes and going on job interviews,

I was like, I'm making a rap record.

Like, why would I waste my time making a resume?

I want to make an album.

So it was like kind of asking direction

I wanted to go in right away.

I ended up signing with a record company

called Delicious Vinyl.

Everybody passed on me

and this one little record company gave me a shot.

And I didn't have met, like I wasn't super connected.

I didn't have like a lawyer.

I know I did it all, I shopped it myself,

but I ended up getting dropped from the label shortly after.

And I got into writing jingles for companies

and theme songs for sports teams.

And that was kind of my first entree into, you know,

I pivoted, it didn't work out for me in the music business,

but I still loved music.

So I stayed in there and I started doing jingles.

And yeah, that's how I kind of started out early on.

You told me you were sleeping on couches,

trying to make it and somebody offered you a tempting deal.

They said, I'll give you $10,000

if I can get 10% of everything you'll ever make.

How did that happen and what was your answer?

Right, so I was writing theme songs for sports teams.

I was 22, 23 years old.

And my business model was to write a song on spec

and then cold call a professional sports team,

try to get a meeting with them,

try to like, you know, get in there.

And then if I was able to get that meeting,

convince them that they needed a theme song.

And that was my business model.

And at the time I was, I was bouncing around

from couch to couch.

I wasn't homeless, but my friends were,

I just moved to New York from Los Angeles

and my friends were putting me up

as I tried to figure out how to do it.

I had no money to go in the studio

to write any more songs on spec.

So I needed money to fund that production.

So a music manager said, you know,

I believe in you, I'll give you 10 grand for 10%

but I want to own you for the rest of your life,

basically 10% of anything you make.

And I was like, I'll take it

because I needed the money to go in the studio.

I thought it was a deal of the century.

You're gonna give me 10 grand

and all I'm gonna do is pay you if I make it.

Like that sounded amazing to me.

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All right, let's get back to the pod.

At the time I was living on my friend, Melissa Katz' couch,

I met her actually at a bar

and she had given me her number on a napkin

and said, if you're in an emergency,

she asked me where I lived and I said,

as of Monday, I have nowhere to live.

I was getting kicked out of my friend's house on Monday.

She said, if it's an emergency,

you can come live with my roommate and I.

Monday, my friend kicked me out

because his parents were coming for a week

and I'm like, this is an emergency.

So I'll just live at get 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 the company called Kinney Park

Kinney Parking Garages in New York

and was, I think the second largest shareholder

of the New York Yankees.

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

What was amazing about that was it really wasn't

and that's why I really was taken aback by,

I knew her dad was an entrepreneur.

I didn't know the extent and she said me on,

by the way, his name is Luke Katz.

He passed away a couple of years ago.

He was an incredibly influential guy in my life

and this was my first encounter with him.

So I went to, not to believe or this,

but I went to see him and it's really relevant

for anyone listening, what he said to me

as a 22 year old, I told him my dilemma,

I'm gonna take 10 grand for 10% of my life.

And he said to me, he's exactly what he said to me.

He said, Jesse, will you make this business work

without the 10 grand?

I said, Lou, I'll mount to something.

I know I can make it work.

There's a, I know I can, and he took his notebook

and he literally threw it on the ground

and he said, I didn't ask you that.

I didn't ask you, can you?

I said, will you?

There's a big difference between can and will.

I know you can start a podcast.

I know you can be a millionaire.

I know you can run a marathon.

I said, will you, son?

And I said, yeah, Lou, I will.

He said, well, tell him to take the $10,000

and shove it up his ass.

Won't make it work.

And I did, you know, like it was a really powerful lesson

and like, you know what?

I signed up for this journey as an entrepreneur.

Let me go figure it out.

Let me go, that's what I want to do.

Let me go figure this out.

And he blew that flame into me at an early age.

And it's really been a theme throughout my life

and all the buckets of my life,

the whole will versus can notion, you know?

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

Well, because it really puts the pressure,

you know, Billie Jean King in a book,

pressures of privilege, and it is.

Like entrepreneur, we play for pressure.

Sean, like as entrepreneurs, that's what we want, man.

And, you know, I recently did a race called Ultraman.

It's a 6.2 mile open water swim,

a 265 mile bike and a 52.4 mile run.

And I thought to myself before the race,

that exact thing, like, I think I can do it,

but I'm never going to know unless I sign up for the race,

put myself in a position

where something incredible can happen or not,

but I got to put myself in that situation.

And now it's up to me, like, will I get it done?

You know, what am I willing to do?

Am I willing to suffer for that one day

to have the next three decades have that in my memory bank

and have it on my resume?

And I am willing to do that.

And I did.

So you know what's really funny?

After you told me that,

so I did a call with you the other day

to just prep for the pod, say,

hey, you know, we're going to talk about,

I'm thinking about talking about this,

this, you have any good stories?

And you told me this will versus can thing.

And the next day, my wife was literally like,

she's like, hey, can you take out the trash?

And I was like, no, no, no, baby.

Thought about can I take out the trash?

I will take out the trash.

And she has no idea what I'm doing.

And I've been doing it all weekend.

I've been, because it's once you see it,

it's actually everywhere.

Ben texted Ben who's listening on this thing right now.

He texted me this morning.

He's like, he's like, hey, how'd you eat this weekend?

We're both like on a fitness cake.

He's like, can you stay locked in from now till Thanksgiving?

And I just, I was like, oh, Ben, you guys could be canned.

We don't ask canned questions anymore.

As of me and Jesse, I no longer ask, can I?

It's will I or won't I?

That's it.

Well, think about how many times in your life someone said,

you say something that you've done, like, you know, I did,

you know, rim to rim, I'll take physical activities

or I climb Kilimanjaro and you explain to someone like,

oh, I can do that.

And I like, in the back of your head, you're like,

yeah, you probably can, but, you know, will you do it?

There's a significant huge difference between like,

oh, just checking the box because you said to yourself,

I can first actually going through and doing it.

By the way, Jesse, I have one other story that you don't know about.

So you used to go to something, at least you went once,

called Coach K's Fantasy Camp.

Is that correct?

I've been there for 18 straight years.

OK, OK, perfect.

So you went to this thing.

So those who don't know Coach K,

he was the greatest college basketball coach at Duke.

I went to Duke and my roommate, Trevor,

used to volunteer at Coach K's Fantasy Camp

and volunteer was literally volunteering.

I was like, so what are you, you're staying over from break

because it's like during some break.

And he's like, yeah, I'm not going home.

I'm going to work this thing.

I'm like, cool, how much you can pay because he's like,

I don't think we really get paid, but, you know, whatever.

Like you just said, put himself in a position

for something good to happen.

And so and what 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 all he was doing was driving the shuttle

back and forth between where you 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, every night he would debrief with me

ideas that he heard.

He's like, oh, this guy said that he does this this thing over here.

This guy said he does this and he told me he goes,

I met this guy, super charismatic, like this guy.

He loved this guy's energy.

He goes and he tipped me a hundred bucks

for this like 10 minute shuttle ride.

And late I told him I told I was mentioning to him

that you're coming on the pot.

He goes, that was the guy who tipped me.

So I don't know if you remember this or not,

but we took that tip and we had a business idea at the time.

And we needed to convince this famous chef in L.A.

to come fly out and partner with us.

We had no money.

And so you you plus a little like a side job that I had became

the money we paid for for the ticket to fly that guy out,

which definitely changed the trajectory of our life.

So little did you know, I love that.

And yeah, I've been going there for since I'm 35.

It's for guys 35 and older.

And it's not to chase some some crazy dream.

It's a combination of, you know, meeting amazing people

and also kind of like there's not a lot of times I'm 55.

So I'm older than you guys.

And I can't stop that clock, you know, at times undefeated.

It's always ticking.

It's it's the six days a year, the five days I go there

that I get to feel like an eight year old again.

And it's really one of the few times in my life

that I get that chance and I love it.

I don't know, man, I follow you on Instagram.

It seems like you live like an eight year old a lot of times.

I'm pretty sure I just I do, I do, I do.

I should say that I'm pretty I'm pretty sure I just saw you

like an RV with like eight friends just like running around the country.

It seems like you.

Yeah, it seems like you got the eight year old life kind of nailed down.

I like to do myself that excuse, Sam.

I guess you put your right.

It's more than once more than five days a year.

Yeah, I think I think you've done that.

All right, you and then it was your first kind of major business.

Marquis jet. So you went from did you go from jingles to jets?

Yeah, so interestingly, I had so the jingle thing turned into a real business.

I found that opportunity.

I started out doing jingles just for anyone that would pay me anything to do anything.

So I was doing jingles for like I honestly like turbo bubblegum.

It's like bubble book gum company that no one ever heard of.

Like just anything that our podcast intro needs a little spruce it up

if you want to if you want to dust it off. Yeah, I got you guys.

And and then I start and then one of those jingles gave me an opportunity

to write a theme song for the New York Knicks.

I had done a commercial radio ad for a company called in the in the paint clothing.

It was owned by Nancy Grunfeld, Ernie Grunfeld, the GM of the Knicks wife.

And she really liked what we had what I had done.

And she said, yeah, if you have any other ideas, you know, let me know.

I said, well, I love to do something for the Knicks, you know, like write a theme song

and we can shoot a video that can sing it in the arena.

So I approached the Knicks to do this song called Go New York Go.

And the Knicks paid me four thousand dollars to buy the song outright.

I'll never forget it.

Like I actually borrowed money to go in the studio to do this to do the song.

I didn't have enough money to go in the studio to record it because they were

paying me 30 or 60 days later.

And by the time I paid the studio, the engineer, the lawyer that I had,

the singer, the producer, it cost me forty eight hundred dollars

to actually deliver the song that they were paying me four thousand dollars for.

And when I look back on it, you know, for most people,

they feel like that's a terrible business model.

It was the best business model in the world for me because when you start out,

you know, people buy into stories, momentum and people very often more than the products.

Like I was the business plan and I would have paid the Knicks ten grand

to say they were my customer because once I had the Knicks,

those phone calls to get into the other sports teams became very easy

and that became my calling card.

So I built a business around that, Sean, that actually I ended up doing theme

songs for almost every professional sports team and turned it into a business

where we were selling CDs like this.

I would take the song as they play in the arena and 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 four 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.

And I moved into my own space.

What was your take home after that?

I had a partner and at the end of the day, I think on the first four million,

I made like a million and a half.

But wait, a million and a half dollars to me.

All the money.

I was Elon Musk.

Before Musk was born, I was walking around like I was Musk.

And a half dollars.

I would go to the wake up at the eight and go to the ATM.

I would get my print out of my balance, swear to God.

Then I would wake up the next morning and be like, are you fucking kidding me?

I have three hundred more dollars than I had yesterday.

And I was sleeping.

I'm like, I'm like, I'll go back to that.

Yeah, I mean, you have a lot of money.

My partner convinced me to take all one point three million dollars

that we both cleared after taxes or whatever it was

and reinvested to get like exclusive deals in all this.

Like we made the business, we reinvested it in the business

and actually made the business a lot bigger and we got our own out.

And then then everything changed a little bit for me.

But, you know, I had no idea to manage money.

My parents never talked about money.

My dad owned a plumbing supply house.

My mom raised four kids.

The thing that I had no relationship with money.

That might sound weird, but like people talk about relationships

with in terms of their relationship with their kids or their significant other,

but not in terms of their relationship with time, which is very important.

And your relationship with money, which is equally as important.

I had no relationship with money.

So when I got money, I didn't know how to save it, how to spend it,

how to use it, how to act around it.

I was very immature around new money.

And, you know, what happened to me then, I lost it

because I didn't know anything about it.

And fortunately, I was able to bounce back

through having other successful businesses and failures.

But no one ever told me about it.

How did you lose it?

Just overspending or what did you do?

Overspending, thinking like, oh, that was pretty easy, man.

I could just I could do that again.

You know, what did you buy?

It wasn't like so much what I bought.

It was just, you know, helping my parents, spreading it out.

I wasn't abusive with it, like, but just I didn't know how to really handle that.

And that's pretty common, right?

Like, you know, Sean and I have a bunch of friends that, you know,

we're both about 34, 35, and we have a bunch of friends and ourselves as well

who had exits at a young age.

And the thing about selling a company, it's different than there's usually

two types of people I've noticed is people who have cash flow businesses

or they're like a lawyer or something like that.

They don't allow for something where your like income is going up a nice amount

every year and you get used to having that cash flow.

And then the other group of people are typically young folks who sell their company.

And typically those people are like me, where I paid myself $20,000 a year,

one $20,000 a year, two year, three was $50,000 a year, four, I sell it

and make a lot of money and you're like, this is just overwhelming.

I don't know what to do with this.

And that's like a pretty that's like a pretty common thing is I don't think

I don't know if most people blow it, but I think it takes about two or three

years to accumulate and kind of get used to and learn what to do.

But there's no one to teach you.

The problem is I had always been taught.

Oh, if you're a like a millionaire was any shit was the no, but I've been

no, I've been taught the opposite.

Like if I saw a millionaire, that was like the pinnacle.

Like he's a millionaire man.

So I was thought like, oh, I have a million dollars.

That's all I need to have for the rest of my life.

I'm a millionaire at 27.

And that's that was the relationship that was wrong.

Right.

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

Yeah, you go on to have a four thousand dollar dinner when you were eating.

When I was basically eating a 99 cent bagel for 17 years, you know, things change quick.

You I'm a big believer that most of life, most of your life kind of is a result

of this conversation you have with yourself and your head.

Do you remember after you kind of had that first hit and you see the money

and you still have your only 27, you still got all your life ahead of you.

Do you at all remember like the conversation you had with yourself?

Like, all right, Jesse.

So like now X and whether X was a good, good, a good conversation with yourself

or misleading one, do you remember what what the conversation you had with

yourself at that point in time was?

You know, it was interesting because shut, I was living in New York

and most of my friends were working on Wall Street.

They were working at hedge funds.

They were making they were making a lot of money around.

There was a lot of money around me.

And, you know, it's very easy to get caught up in what's he making

versus what am I making?

And it's very easy to like you start having those conversations with yourself.

You can go down and spiral downward very quickly.

And, you know, what I was making, what it took me years to make and build and sell.

And my journey to get to that point was crazy.

I was selling carrot and celery sticks door to door.

That didn't work.

I had a t-shirt company that didn't work.

I got dropped from a record label.

That didn't work.

I saw I cleaned meat drops.

That didn't work.

I sold chicken shrimp and meat door to door.

That didn't work.

I mean, Jingle company, it went on and on.

So, you know, I had really worked so hard.

And and at the same time, like I had invested so much, not for the money, but

just like I just wanted to get a record deal, man.

I didn't care about the money.

I just 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 worked with

Laird Hamilton and you were saying how that he was saying how that, you know,

you're one of you guys saying you need that anger to inspire you like 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 never want to lose that underdog mentality.

I never want to be like, I'm at the top of the mountain.

I'm not.

I consider myself back of the pack.

Everything back of the pack sales, back of the pack entrepreneur.

There's so many better entrepreneurs than me.

So many better salesmen than me.

But I, I, but I love that feeling of I got to prove myself.

So when the money happened, it was just like, oh, Steve Stark is making

so much more than me.

We're in the same basketball run.

Like I got to catch Stark, you know.

The, um, the marquee jet thing, that's interesting though, because that's

like totally out of left field.

So, and that seemed like a way bigger win than the jingle business.

Same partner, right?

You're saying the same co-founder?

Yeah.

Same partner.

Um, it was a much bigger win.

And it was 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 have it been in my business plan.

They've been opportunities that presented themselves.

You know, my whole life I've been taught when opportunity knocks, you know,

and I'm not, I don't want to sit around waiting for opportunity to knock.

I like to create my own, my own opportunity.

And I was a guest on a private jet with my partner.

And I was like, people fly like, what is this?

So what is this that I'm on?

And we led to some research, like there's only really two or three

ways to fly privately back in the nineties when we started marquee jet.

You can buy your own airplane if you have $50 million, you know, or something

like that.

Well, that's out of the question.

You can get a fractional, be in a fractional program like net jets, but

even that is a really big commitment, both in capital and time.

It's a five year commitment, a lot of money up front.

That wasn't, I mean, that wasn't an option for us.

Or you could charter.

And there were a lot of questions around, well, who owns the plane?

Who are the pilots?

You know, do I feel comfortable on that?

What if the plane doesn't show up?

So we found the little white space there and said, you know, we only

want to fly like 25 hours a year.

I bet there's a lot of people like us that don't want to own an airplane.

Don't want the responsibility, but they just want to be able to have the, um,

have a plane available on short notice.

And that was the idea around selling a 25 hour jet card that worked like a debit

card.

So if you, if you and Sam Sean flew two hours, you'd have 23 hours left.

And then we partnered with net yet again, part of being an entrepreneur is

figuring out how to get from A to B, the fastest.

And for us, for me and my life, many times it's been through partnership.

We partnered with net jets.

They ended up buying us to use their airplanes, partnered with Coca-Cola at

Zico, at Zico Coke and order.

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.

Where do we go for airplanes?

And, uh, and then started that journey of, of building this company.

So you walk in, you walk into net jets and you're like, Hey, um, I'm Jesse,

former rapper, jingle,preneur, and I would like for you to give me your most

valuable assets, your planes for this new membership program.

How did you convince them to do that?

Well, at first we didn't, they kicked us out of the office in the first

meeting after about 12 minutes.

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 a thousand on their SATs into a room to pitch them the idea?

A year before that, I was a yes guy my whole life.

I was, I, I've kind of, and I still try to pride myself when people ask me

for things to deliver if I can, but never asked for anything in return.

You know, like, I'm not like, Oh, Sam, I'll do this for you.

Sean, but like, can you do this from like, I don't know, that's not the M.O.

I got a call a year before that from someone that said that their daughter,

this is a true story and it's the craziest story ever.

This guy was having a, his daughter is having a sweet 16.

And Chris, um, a famous singer was performing in his hometown.

His daughter wanted to bring her sweet 16 to the event.

The guy says, I know, you know, the manager, can you help help this guy get

some tickets and do anything special?

Turns out I get the guy's daughter as a backup singer for one song with the mic off.

Everyone in school, the next day is, well, she's like the hero of this.

Like, what happened?

Oh my God, they're freaking out.

The guy calls me up.

He goes, I don't know who you are.

I don't know what you have, what you do, but you lit my daughter up.

And if you ever need anything, let me know.

Like, turns out he, I can't make this up.

He's the president of that jets a year later.

I need 650 airplanes.

I call him up like, Jim, you're never going to believe this.

The guy who got your daughter, I have an idea for a thing.

He gets me the meeting.

We get thrown out of a 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 goes, you know what?

That was amazing.

I said, we got thrown out in 12 minutes.

What do you mean to me?

He goes, Rich Santulli, my partner, he doesn't give anyone 12 minutes.

He goes, there's something he come back next week and bring this thing to life.

We 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, but every guy sees 100 PowerPoints every year.

We brought in our own focus group.

We'd ate people in the lobby and they walked in one by one and they stood up

and said that they would never buy a fraction of an airplane.

What Netschets was selling, but they would buy a 25 hour jet cart.

And at the end of the meeting, they literally said, if you guys raise money

or put up your own money, if you can figure it out, we'll give you a shot.

And a couple of years later, we had more customers than Netschets.

That's crazy.

You showed him the market.

You were like, I could either put up a chart or a pie chart right here.

Or I could literally walk the market into the room and have them say, I need this product.

And it turns out that eight people saying I need this product to your face

makes a bigger impact than a pie chart that says 11 percent of the market needs this.

When I think back on this moment at 28 years old and we had like Carl

Banks from the New York Giants, I think Run from Run, the MC was there,

was right behind me on the wall.

You know, these guys at that meeting.

Yeah, we brought it. We brought it in.

We brought him in. And when we said 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 much older corporate client.

And what they realized, I think, in the meeting was here, these two 27 year old kids.

And by the way, remember, I said, people buy into people's stories and momentum.

This had nothing to do with our product.

The decision maker looked us in the eye and said, I see enthusiasm.

I see someone that's no matter what, even though they have no aviation experience,

is going to make this work.

And I'm willing to bet on these two guys.

It wasn't there was no PowerPoint.

It was us, like, you're the business plan, you are the business plan.

So at the end of the meeting, he literally said to us

after we got the deal and like year one, we did I think we did like

close to 200 million in sales year one.

And I remember going into his office and asking, I said, Rich Santuli,

who is like, he knighted me, man, he knighted me.

I said, Rich, how do we how do we end up here, man?

And he looked me dead in the eye and he goes, you guys remind me of me

when I was 27 and bringing in this focus group.

Yes, they came in and they explained why they would buy a card.

And yes, they saw a much younger demo that someone could be

a lifetime customer now at 25 versus a lifetime customer 50.

So they saw the lifetime value of what we were bringing in this younger

generation of athlete, entertainer, you know, young mogul, etc.

That they wanted that because that's incredibly valuable to get

that person on their plane at a young age.

But at the end of the day, they he saw something in my penny

and I and my partner and I that he wanted to bet on.

And, you know, I just want to say this for anyone listening here

because I know this is primarily a business podcast.

By the way, it took me 37 minutes to warm up, but I'm fully here.

He's here. I'm slow today, but I got it now.

Um, you know, like I said, that was never in our business plan.

Oh, we're going to bring in our own focus group to start a company

that does five billion in sales.

It's like it's the things that live off the business plan

that make the biggest difference.

And when you have a chance, you know, you don't get a lot of big meetings like that.

And I remember 27 walking in there and saying to my partner, like,

this is as big as it gets because, you know what, there is no one else.

It is 650 airplanes.

This is it.

And, um, you have to bring that meeting to life.

You have to stand out.

You have to, you know, not in a gimmicky way,

but you have to make that memorable, man.

And, and fortunately, we were able to do that and it worked.

And then we had an amazing, amazingly fruitful relationship

and partnership with net chefs until we exited.

Are you so like, I think that all three of us might be a bit similar

in business relationships where we're like, we bring the passion

and some of the creativity and the zero to one stuff.

Were you good at running that company?

Or were you, or did you have a good partner who was running it?

And you were great at kind of bringing some of the deals to fruition.

I can only run marathons.

I can't run any business.

I'm not going to run 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 OK with it.

So, you know, we were able to hire a CEO right away.

And then, which allowed me to focus on sales, which I was, which I was better at.

Buzz, which I was really good before the, before Instagram.

I'm not so good at the up now with Instagram, but back when there was no Instagram,

I was good at creating pureable opportunities and, and talk worthy events.

And for my year, that was really important.

So, no, I have never, I've never been the CEO of a business.

I've never ran or operated a business.

But I've been a founder, I think, five times.

And how did that model work?

Is it like a Costco model where you were breaking even on the 200 million

in sales, but you made money off the membership?

No. So we, the original deal with 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, if Sam, Sean, you guys bought a hundred hours,

we'd go buy a hundred hours and it was marked up.

So we were just a marketing organization.

They owned and operated the planes and we were leasing it as we got big.

All of a sudden we have a 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.

It was a true no lose for both parties.

And that those headline numbers are really big.

How big was that exit?

I mean, that's a that's a pretty big thing.

How big is NetJets?

I don't even know.

I don't even remember what NetJets sold to Berkshire for.

I'm sure it's public.

This was before Berkshire owned it. Is that right?

NetJets sold at the Berkshire prior to us.

And then and then we went to now we're part of that.

Now Cheejet's not part of that which is Berkshire stock

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

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

NetJets sold for 725, 725 million in 98.

And half of it was paid in stock.

So that was if that was a good deal for NetJets, depending on

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

You you snapped your fingers

and you were like we did first year we did whatever.

I forgot what you said, two hundred million or so. Two hundred.

I don't know what that means.

What is two hundred million there?

That's not that can't be membership dues.

That's that would be insane.

No, it is. Yeah. No, because our average our average customer

spent close. I think it was two hundred and fifty or two hundred

thirty five thousand dollars a year. Gotcha. OK.

And it's more like a GMV.

So because you have to to your take is some spread between that

and then whatever NetJets. OK, gotcha.

So yeah, I guess like on that model, what's the income on 200?

Let's just say a hundred million.

What can your profit be on that?

Well, this is 30 years ago.

So I don't remember exactly what it was, but it was enough that I was now off

the couch and living a very good life.

And and by the way, the best ROI in that deal is I met my wife there.

She was a customer of ours, and that's how I met my wife.

You you said you told me something

which was about getting the first customer.

So before your wife was even a customer, you know, you're like, I'm on this plane.

I'm like, holy shit, this is an amazing way to fly.

I'd love to do this.

I'm sure other people would love to do this.

You come up with the idea. Cool.

Now, how do you go get those first people

to give you two hundred thousand dollars to be a part of this, right?

That's like a huge like where did you go find those customers

and tell the story of kind of how you got it off the ground?

Well, we were start we started out, you know, I think the first thing

that any entrepreneur, most entrepreneurs, at least in our position

and at Marquise, it is we had to establish credibility

because if I was going to sell your 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 will leave.

But if I was like, you know, Oprah, Bill Clinton,

you'd be like, wow, they must have vetted this, you know.

So we started out looking for athletes, entertainers and high profile people,

which was not easy for me.

But I had to go where wealthy people congregated.

And I heard about this, you know, they could afford time on a jet.

I heard about a conference in Monterey, California

that was just getting some traction called 10.

So I go out to Monterey and I told the guys like, hey, I'm going to go get my first sale.

I'm going to think of the head talk.

They were like, what?

You know, and it's in Monterey, California.

You got to like, you can't even get there.

You have to like connect it through Chicago into whatever rented a car

of five hours of Monterey.

I get to the 10.

It's like Fort Knox, man.

Everybody has a credential, like this is like huge.

And I'm like, you need a credential to get in here.

There's no credentials to be found.

So I'm thinking like, how am I going to sneak in, buy someone's pass,

like go into the room where all the qualified leads are.

I'm in this coffee shop plotting, like, you know, my my my entrance or how I'm going to do it.

And every two hours, a wave of people come in and they're buying.

They have these credentials.

I'm like, oh, this is where they come on their break.

And they're all buying lattes and muffins and these lattes and muffins and whatever.

Latte's and muffins.

So the next morning I got up at five and I bought all the muffins from this.

I controlled all the muffin inventory in Monterey, California.

And I literally just waited.

And this is a true story, by the way.

And it's been verified.

You can walk.

So two hours later, this guy, the first wave of people on the break walking

and the guy orders a latte and a muffin, I stop them.

They tell him that they could give him a latte, but they're all out of muffins.

It's like fucking nine in the morning.

He's like, you're out of muffins.

The guy starts walking, I stop them.

It's sorry, I overheard you.

I actually have an extra muffin if you want to muffin.

And he's like, you got an extra muffin.

I'm thinking like, I got every single fucking muffin under the table, man.

What do you need?

And I started talking to him.

He's like, you know, what do you have here for the conference?

I'm like, me too. What do you do?

I tell him what I do.

He said, you got to be kidding me.

I'm in the market for a private jet card.

And his name was Josh Koppelman.

He owned a company called half.com.

Famous VC.

Right. Now he is.

I bumped into him like three years ago at a retreat.

And we were talking about this.

And anyway, he was my first sale.

He was my first sale.

And that is not a story of me being a good sales rep.

Because like I said, I am truly back of the pack.

But it is an example of me putting myself in a situation,

Will vs. Ken, of putting myself in a situation

where I could attract that kind of luck, you know?

And and he was my first sale, though, showing to answer your question.

And you know what happened after that?

I'm going to tell you what happened after that.

I serviced the hell out of them.

I did what everybody listening would do,

but I did 30 percent more.

So when he went to Mexico, he expected me to return his call

and every DM and all that.

Of course, I did what everyone he would do.

But he went to Mexico.

He didn't expect the list of pediatricians that I vetted

in case his kids got sick.

He didn't expect me to make reservations every Wednesday

at every night at eight o'clock during spring break in Mexico

in case he and his wife wanted to go to dinner.

And 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 operator.

I was never the COO.

I was I wasn't even I don't even think I was on the org chart.

So I'm 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 the 2005 version of Marquis jet.com.

And I'm looking at your about page.

And what's interesting, it looks like your senior executive team

was not only awesome, it was like amazing.

Because Ken Austin, I see, was your executive VP.

Is that the same Ken Austin that went and started

as an avion, the tequila company, and most recently started

proper 12 with Conor McGregor?

Is that the same Ken Austin?

And the tequila company with the rock. Yes.

You've done a good job of hiring.

No, we were the Boston Celtics, man.

We were the Boston Celtics.

We from like the old we the talent

at this company was exceptional.

Ken Austin is an exceptionally.

I don't he could be the is such a talented guy.

And I learned so much from Ken and, you know, we had great sales reps

and we attracted really good talent because we built a really good culture.

Well, it's also a sick product.

I mean, you said you met your wife there.

It's like that's like the greatest line ever.

Like, oh, do you you're here at this jet company?

So I know like you're of someone I know you're someone interesting.

Definitely just so happens.

I work here or I own the company.

I mean, it's like that's that's it's a pretty wonderful experience.

I imagine to work at a private jet company.

It was it really was and you nailed it.

But the only thing I would say to that is I think there were like

sixty five 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 if something some including Garrett Camp, the guy from Uber,

he created he tried to do an Uber for jets that didn't work out.

Right. It's very, very difficult.

And if we didn't have net jets as a partner, you know, it went to

I'm sure it wouldn't have worked as well.

So a lot of things lined up for us.

The business you did a partnership on was Zico Coconut Water.

And I think this is interesting because now we're seeing a pattern.

The first is you're picking businesses in like categories

that they're not in the NBA curriculum.

Nobody's thinking about, oh, sports teams need slogans and CDs

that will increase their fandom.

Nobody even realizes that that's a niche that you can go into or to do,

you know, this membership model for private jets.

Nobody's even looking in that area at the time.

Right. There's a very few people are even thinking about that niche.

It's not common. Then you go coconut water.

So now you're consumer packaged goods in a beverage category

that's non-existent really at the time.

And I think Zico was pretty small when you found it.

It's not like it had like, you know, tons of momentum.

So talk about two things.

Number one, finding these niches.

Like what is it that you what is your operating philosophy

that leads that seems to consistently lead you to these?

That's the first question.

And the second is the key partnership that got it off the ground.

I heard an amazing Matt Damon story.

I want to hear the full version of it.

What was Zico? Yeah. Yeah.

I spent a year trying to figure out how to have my own coconut water company.

I went to Brazil. I went to Jamaica with trying to figure out this is

there were no there was no coconut water in the store side.

This is I'm so let me back it up even further.

I was running a hundred mile race

and I did a lot of trick when I was doing my training.

I did a lot of research around hydration and nutrition.

If I'm going to run for arguably 24 hours,

how many calories do I need to eat, drink an hour?

How many calories do I need to take in an hour?

How much fluid ounces do I need to drink an hour?

How much salt do I need an hour?

And my research led me to coconut work.

So I ran this race powered by coconut water

and I finished it in 22 hours and 30 minutes.

When I was done, I'm like, this is going to be this is the new Gatorade.

No one knows about this on the human guinea pig.

I'm bringing this to market, you know, it's a better option.

It's all natural. One ingredient, you know, it rains.

God sends it up a tree.

We crack it open and we drink it like this is.

I mean, are you kidding me?

So I spent a year trying to figure it out, how to import it.

And I realized like I did get an I needy on my SAT

because I couldn't figure it out.

But I knew I could market and sell it.

I knew I could.

So again, same model, same formula.

I took the idea to Coca Cola.

The president of Coke's emerging brands division

was friends with one of my customers at Marquis Jack.

He got me a meeting.

I pitched the meeting.

In the meeting, I pitched this idea of coconut water.

He takes the liking to me, but he says, we don't buy PowerPoints or Coca Cola.

We buy brands.

He goes, but if you partner with another company or something,

you know, maybe we can then out that that's out there.

There's proof that they can make the product, ship the product,

get it in stores or whatever will come in.

We'll partner with you.

So I went to Ziko and that's how we formed the partnership.

During the meeting, the about a week before I was at

Matt Damon's house and Matt was also a customer of a Marquis

jet and I did the things that I did for Josh Koppelman with Matt and we became

friends and I said to Matt, you know, he'd asked me if I wanted to spend the night.

They were going out and I said, I'm going to Brazil in a day or two.

I can't see was what are you doing in Brazil?

I said, I'm starting a coconut water business.

He's like, you've got to be kidding.

He's like, I love coconut.

I have a coconut tree in my backyard.

He's like, I drink because if anything happens,

what, you know, with this company, let me know, I may want to get involved.

A month later in the meeting at Coke, like the meeting is going so bad.

I'm showing this PowerPoint, you know, like and out of nowhere,

like I know I had achieved the whole feel of the.

I just turned to the president of the guy at Coke and I'm like, you know,

my partner, Matt Damon and I and the guy went, Matt Damon is your partner.

I said, I didn't mention that.

What are you talking about?

We go all the way to the one yard line.

I leave and I call Matt.

I'm like, Matt, I need a favor.

He's like, I'm like, can I come over with the cat?

Can we climb up your tree, get a coconut, chop it open, you know,

go in the kitchen, put a straw in it, you know, turn to the camera and say,

Moutar, Moutar, Kent, the CEO of Coke, there's got to be a better way than this.

He's like, all right.

And I filmed this.

He filmed this award winning frigging 35 second short film of him getting

a coconut, chopping it open and saying there's got to be a better way.

And, and we got the deal and the creek, you know, what's interesting

about that is obviously who's going to get, you know, a megastar to come.

That's not the point.

It's it goes back to what I said, will you make it work?

Putting yourself in a situation where you can get lucky.

Here's the other pattern, Sean, you're talking about patterns

and making me making yourself stand out and be memorable in a meeting.

Now I stretched it a little with this one, but, but, but it ended up it ended up

working out. That's an amazing story.

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

I love that story. I love that story. You.

That's wild.

I like Coke bought it two years later, 100 percent.

Did you when you bought, did you buy into Ziko at the time?

Like, did you was that like a. Yeah.

And have you made bets that you felt like financial bets that were risky?

Like, you know, Elon does this thing where he sort of rolls all the proceeds

into the next business and sort of re goes all in each time, which is, you know,

probably not advisable to most, but like, what's your strategy been now

that you have some chips to play with?

Do you do you make big financial bets?

Are you saying, no, no, I'm going to add value strategically.

Do you start things from scratch?

What do you, what do you like to do with the chips that as you accumulate them?

How do you, how have you used that to your advantage?

Well, I felt I realized that I've got, as I've gotten older,

that more isn't better, better is better.

And I really don't make a lot of bets.

I have four kids.

What I'm most proud of showing in my journey at 55 is that I've been,

I've exited five businesses, but I've been able to keep,

build a family, keep my health, you know, be a really good son to my parents.

I have great friends.

So I really aren't, I'm not, and I'm not using Elon as an example.

You brought him up, not me, but I'm not trying to roll everything in or

I'm really proud of what I've been able to do.

And I'm really proud of the life that I built.

So I really don't, I really say no to most.

I have this thing at this point in my life,

if it's high aggravation for high reward, I'm not doing it.

If it's, and that goes for anything, money, friends.

I don't want high aggravating friends.

I'm on friend reduction right now.

Come on, friend reduction, man.

I want a low aggravation.

You're doing layoffs.

You do Zoom calls with people, let them know.

I'm sorry, we had to make a reduction in friendship.

We're doing layoffs.

Excuse me, Mr.

Damon, can you step on my office?

There's a separate package.

We'll hang out three more times, but that's it.

We need to have a discussion.

That's great. So fun.

More MFM in just a minute.

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All right, let's get back to the pot.

I'm not trying to, you know, push you really.

It's like it's based on my enthusiasm for something.

How's it going to impact my life?

Meaning like day to day.

I walked away from several ideas that I think could be really good.

She goes, because you're like, just because you have a good idea doesn't mean

you should do it.

And I've, Sarah said that to me, I had an idea.

Now I see people are doing it now about eight years ago.

I said, Sarah, I have an idea that's bigger than Marquis jet.

Like Marquis jet was the biggest thing I'd done, you know.

And I walked you through it and she goes, that's an incredible idea.

Don't do it.

What was it?

I wanted to take this is going back eight years ago.

So now it might sound like, oh, well, people are doing it now.

I actually pitched this to a major airline now that's doing it.

But I wanted to make commercial travel feel like private travel for people.

I felt like there was a bit and there still is an opportunity for people

that would pay up to fly commercial.

But they want an experience that's more private.

So for example, if I'm flying from New York to California,

and I'm by myself and I'm on a global or a gold stream and I'm going around

trip, that's an expensive flight, man.

That is an expensive flight where I could just buy a first class ticket

for maybe 1500 bucks.

So instead of let's say that that that flight cost me, if you

chartered it, maybe it's going to cost you, let's just say $50,000.

It might be more, 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 1500 bucks.

I, as a $1500 ticket holder, would gladly give you another $1500,

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

it through the back door.

And no one was doing it.

No one was doing it.

And now they are doing stuff like that.

And that's why it's like you like unbundled the private experience.

It's like, OK, there's the jet part of it.

But then there's the walk on to the plane.

Walk off the plane.

Everybody wants to get on an airplane.

Do you really care?

Yeah, it doesn't matter.

I'm in one A. No one's bothering me in one A.

And in some regard, the commercial jet is safer.

You have more amenities.

So yeah, like, but I've been on a I flew first class

from New York to LA one time for like some meeting.

I would never flown first class, but I did it because it was overnight

and I had to be ready for a meeting.

And I get on. I was one A and one B are sitting next to me with Stephen A.

Smith. And I was like, how the fuck do you go to the plane before me?

And I like looked it up and apparently there is like a private door.

I guess if you're famous, what is that?

Well, I think now several airlines have and there's services

that do it outside of the airlines as independent services.

But my point is so I had the idea,

but I also felt like I had the buy side that I could deliver to the airline

because, you know, I'm involved with them with some NBA players

and I'm part owner of the Atlanta Hawks.

And so I have I have and my friends are all doing really well

that are that are all doing really well.

I thought we'd want to have this service.

So I had the idea and a significant part of the buy side

to package together to an airline to bring private flyers onto their mothership,

which is the domestic part of their travel.

But but anyway, to answer your question, so things like that.

Good ideas, lucrative, but does.

But for me, at that point in my life, to put, I feel I don't know

if I have the energy to do it.

It's going to take away from Tuesday's flag football game.

I'm not doing it.

And I don't know if I had that.

If I still have, I don't, I don't still have that.

Well, you but you can't turn that switch off, right?

Because I saw you on Instagram, like, you know, I don't know, a year ago

or six months ago or something like that.

And you were like, pickles.

It's you're like, guys, pickles.

And, you know, it seemed like, you know, the guy who was saying

coconut water when nobody was talking about coconut water, he's talking about pickles.

So me and Ben start paying attention.

We're like, Hey, what's Jesse?

It's a deal with pickles.

Well, OK, he's kind of right.

They don't brand in pickle.

And so describe this pickles opportunity that you see now currently.

This is a present day now, right?

We're done with the past.

Now we're talking present and future.

What do you see in the pickle market?

Well, like 245 million Americans eat pickles every year.

It's like 75 percent of our population eat pickles.

And again, it goes back to the to our running conversation.

I'm starting to see at races, pickles at the at the at the aid stations.

They never existed 10 years ago.

Pickle juice never existed 10 years ago at at the aid stations of Marathas

and your local five help you with running.

Yeah. So that made my intent was that it has a lot of salt in it.

When I grew up, all my black friends would say that they would drink

pickle juice in order to avoid a hangover. Oh, yeah.

In Russia, it's a it's a you know, it's a big remedy for hangovers.

But my point is like it put my antennas up.

Like, what is this, you know, just like when I saw the first thing

of coconut water on a shelf, I was like, what the hell is this?

I just ran 100. I'm going to.

So so I started doing so I started thinking about it.

And I'm like, you know what?

I can't even name three pickle companies.

And I love pickles.

I don't even know.

By the way, this is the part where he's going to bring in a focus group

of 10 people and he's going to say they have a pickle company

and nobody can do it.

And he's going to be like, that's the business plan.

Well, listen, so I I I researched like the seven best tasting pickles

and the seven best tasting pickles.

I think it was like the today's show did or something.

You know, it's like it's like someone credible did it.

I only knew one cup one of the companies.

So I'm like, if I only know one of this top seven best tasting pickles,

there's a problem in the marketing of pickles.

It's a marketing problem.

And I'm a good marketer.

So that's where it started.

And I'm like, this is a category with no innovation, no fun.

You know, 75 percent of Americans eat pickles.

The average American eats like 10 pounds a year.

That's more than cereal.

And I'm like, I like it here.

I like this space.

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

Same. Is it Clausen, like the big brand?

Is that right? I like Clausen.

I like Mount Olive.

Is it called a Valsic or Vlasic?

I like that company.

But I think Mount Olives is the biggest ones.

I always get the little ones that look like a witch's toe.

You were in a mental on the pickle shirt.

I'm not. Look, I'm not I'm not I'm not big.

This is a big pickle around with a clatter.

Won't just expect to that company, right?

I don't even know.

But I'm just saying, like you ever see me

when we're in the hatchery? Oh, my God, it's like I'm convinced.

In fact, we're texting Mr.

Beast right now. We're going to come into this market, too.

You just made a mistake, my friend.

You're we're bringing our car influencers into this market.

I believe you on this opportunity.

Why do you know?

Let's just let's get the beast on the phone.

Let's partner with the beast.

Beast people. That's right.

That's right. Who needs Matt Damon?

Well, we got Jimmy now.

Ma, yeah, where's David?

I need to go get Ben Affleck.

He seems like a good pickle guy.

I need to know about feast is low aggravation, though.

I only want a low aggravation.

I don't know about that one.

My olive does two hundred twenty million in revenue a year,

privately owned.

It sounds it sounds doable, man.

Sounds like our money, right, guys?

Yeah. Yeah.

I want to thank them very much for holding it for us.

Shoot a text over to the CEO of olive

and let him know to keep that money for us.

All right, we'll be there soon.

What other ideas you got?

Because I told you, I said, you know,

you'll get this because, you know, you're a you're a rap guy.

When you go on certain shows like The Breakfast Club

or Sway in the Morning, there's like an expectation like,

OK, if you come on here, you've got a freestyle.

And we're trying to do that of the business realm.

It's like, you come on here, you've got to bring fresh ideas.

You can't just only talk about your history.

And you go, you tell me, you go,

I got 50 ideas at my top drawer.

I said, all right, say no more, but you hit it at me.

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

Sweet gherkin, bread and butter, kosher dill.

Like these are all rap names, man. Yeah.

Yeah, we're about to have those pickles.

All right, tell me tell me about this idea.

You gave me three words.

I don't know what the idea is, but you said,

ready made eight ounce drinks.

What you got in mind?

Yeah, so I mean, I've been accumulating ideas in my in my top

drawer for 35 years.

I love starting them, Sean, you know, but

yeah, I mean, I don't mind.

By the way, if you guys want to rub anyone wants to run with this, you can.

I think a one penny royalty, I'll give it to charity.

You know, I think like I go back to five hour energy.

The brilliance of five hour energy is they took a, you know, 12 ounce

energy drink, they shrug it down to two and a half ounces, right?

That's what five hour energy was.

And why did it work?

They they only I believe I believe they only a predominantly sold stores

that would put it on the countertop when they started out.

So like it wasn't buried at GNC on the bottom shelf.

And it was like on the countertop at checkout impulse buy.

They were selling 10 million two and a half bottle ounce bottles every week.

10 million when I look at when you look around retail

at the counter at checkout of retail, the countertop is incredibly crowded.

And you go to Whole Foods, there's gum, there's mints, there's this,

there's that, there's chocolates everywhere you go.

Gas stations, there's lottery tickets and the only place

that I found like where there's open area or liquor stores.

If you go into a liquor store, you don't see that the the the

self state, you know, the stands and the crowded space and all the

Choskies and stuff that you see at gas stations and at at grocery

and and other retailers.

And I think there's a tremendous opportunity.

I was going to call them quickies to have like ready made shots.

Same thing as as five at like of your wool, lemon drop, whatever your

favorite kamikaze ready made drinks are right at the countertop

that are already made fresh ingredients, you know, where people

could just come and grab and go and have a ready made cocktail

that they could bring to tailgates, parties, et cetera.

I'm not saying it's going to it's going to be a great goose vodka,

but I see an opportunity.

And if not that, someone should go make a deal and in a very fragmented

he now you got me thinking, Sean, now I'm not in this with you on my radar,

but here we go.

Like the freestyling should be talking about us point that

on really even a better idea would be to go.

Liquor stores are that is the most fragmented market out there.

They're all mom and pops.

There's no like chain of liquor.

I mean, you 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 go rent.

The countertops of all the liquor stores and then go to Nabisco,

one of the big boys and be like, hey, guess what?

I own 10,000 countertops.

You want to put your widget there?

You want to put your fucking widget there?

Keep the money one.

Yeah, keep the money one.

Oh, I love it.

Yeah, the real estate.

Probably we could probably talk for 15 minutes about the opportunity

and come up with 10 ideas around that.

You know, that's where it starts.

It starts with just like bad idea or better idea, the idea.

Yeah, exactly.

Exactly. And you're kind of like, I think the background of rap.

I'm not I'm not joking by this.

I think the the way the brain can sort of like not censor itself

and wait till it has a fully formed, perfect idea,

but actually just start to go and then know that I'm going to hop from this

to this to this to this and there. Yeah, that'll be the line.

And that's all I need to do is get to that one, that one line.

I'm going to show you this too.

This is this is something I'm selling now.

This is I don't know.

Are we on are we on YouTube too?

Are we on there all in our video, video, video?

This is by 2024 all planned out.

This is next year, fully, almost fully baked.

What my year looks like, my races, my what's orange?

There's a lot of orange on that.

What does orange stand for? Orange, orange are.

So when Sarah sold Spank, she wanted to do a lot of traveling.

So this year, we committed as a family to go on the road.

So all the orange, as crazy as this looks, is all travel.

We're going to Africa, we're going to New Zealand,

but it's all mapped out yellow.

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

Yellow on my races and events.

Green is my speaking.

Green is our birthdays and stuff.

This thing's dope.

Not I wanted to ask you about this because you are super legit

as far as like what you've actually been able to accomplish

your level of success.

And you do stuff like this.

You have like the big ass calendar club or whatever.

It's like that thing is called Big Ass Calendar.

That's a product you make.

It's like a course you have.

And I was surprised that you're doing those things.

And, you know, what's what's your thought process on like or the running

club or the running club?

Like, how do you pick projects?

Yeah, I mean, I think this goes back to the earlier question

you asked me about reinvesting in other businesses and stuff like that.

How old are you guys?

How old are you, Sam?

Thirty four.

I'm thirty five.

So I got I got two decades on you guys and but I got I got the most

experiential decades, I believe on you guys.

You're the forties and fifties, thirties, forties, fifties.

You know, for me, there's I'm in a coaching space, you know,

you know, I speak a lot.

I have coaching programs, the calendar, but even the events that I do,

the run running races and this kind of stuff, it all has an element of getting

people to do more than they thought to inspire people to do more than they

thought they could.

But but to answer your question and the reason why I just said that is.

The gal works with us in our family office was looking at all the businesses

and and asked me like, I don't have a sales rep on my payroll.

I don't I'm not going crazy on the marketing and this and that.

And it's really word of mouth.

And she looked at the numbers and she's like, you know, do you want to scale

this and what are you doing?

Why don't you just go do the liquor idea or the airplane idea or this idea or

that idea or any of the ideas in your draw.

And I pulled out my phone and I said, Kendall.

All these are from today.

All of these messages are for today.

Pick one.

Reddit, I said, I can't and it was like, you changed my life or this is really

inspired me or you know, I did this or I saw my parents.

I haven't seen my parents in a long time.

And you know, I talk about the importance of that very often, you know,

about not losing sight of what you already have while you're chasing your

entrepreneurial dream, your health, your family, your friends.

There's no business in the world that would give me the return on investment

that I'm getting right now.

There's nothing I could do.

What build another marquee jet or 20 hour days?

I mean, like that's not going to 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 is a wire.

You get the wire and it's like the same feeling you get when, when you sell a

business is the same feeling you get when you finish the marathon, 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, 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 like what you would, I don't, I don't know.

I'm just enjoying how it's making me feel right now.

And what's wrong with that?

I got to scale just to scale because everyone told me how to scale.

I don't want to do that, man.

I did that.

So a question that we like to ask people is it's a really simple question, but

we, we learn a lot, which is like, what do you do with your money?

So like you have a really interesting lifestyle.

I agree with you.

I'm not, I don't like the Elon Musk path of all these sacrifices and doing

things for the sake of humanity.

I'm like, I'd rather have a fun life and you have a really sick life.

I mean, I, 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 this, are you just, are you using your

speaking fees to finance it?

And then you have your marquee jet money and just one big account in the, in the

markets, how's your portfolio set up and what are you doing with your money?

Well, just, you know, it's, um, I don't know, man.

Like we, we, we never really think about it that much.

I know that's, I don't want to delittle it or sound in any way.

I'm not just, 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 quite droop a lot of money.

Like we don't really think about it.

It's like it's spread out strategically and we live our life.

What's your monthly burn?

I mean, what, what does one need to spend, uh, per month to do that?

I like to ride my bike.

I like to run.

I like to swim.

I like to speak in public.

I like to be around my family and friends.

What, whatever that costs me, Sam, is what I'm going to spend on it.

How's that for an answer?

Yes, Sam.

Um, I want to ask you about something that you have talked about that I really

liked, which is, uh, around your life philosophy.

So you have a few of these that have made an impact on me.

You, um, I don't know where I saw 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 phrase it, but it was like

comp, you go, I can network in three minutes, right?

I can, I can invest in my friends, my fight, my network in, in just three

minutes a day.

And I'm always interested in anything that's like, you know, the six minute abs.

I, I tend to be interested in the like, you know, shorter timeframe type things.

And you go compliments.

What was the other ones you go compliments, um, complimenting.

Can graduate and console explain 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, actually like a very effective little tip.

I want you to share it with here.

Well, in my twenties, I didn't have a way to, I had no, I was really on a super

tight budget.

I was writing 10 handwritten letters.

I went a year, not every single day, but pretty much writing about 10

handwritten letters a day.

And that was my entire marketing strategy.

And I realized that, you know, it's a great way to get through the clutter of

email, DM, social, you know, all this stuff.

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 have sent the text.

You mentioned the cake had in me, coach K.

I sent a fluid to Carolina, um, that's too long ago.

And I said, coach, a text thanking him for having the event.

And I said, you know, you have to respond.

I just want to let you know, like it makes me feel like an eight year old for

five days a year.

I want to thank you for, for doing this.

I know you don't have to do it.

And it took, and like, I realized like, he might share that with his team, like

grabbing an impact, 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 them and say, coach,

I send you a text.

Like, I don't know if you got it, but like, I add that permission to do it.

I'm not coming out of left field.

Like, Oh, hey, coach.

You know, like, well, you just, so that took me 45 seconds to hit sent,

write it and hit sent.

So I was like, okay, if I did three of those a day and just took three minutes

and just started hitting friends, suppliers, manufacturers, inflict whatever

over the course of the year, often a thousand, I will plant a thousand

permission slips all over the country and world three minutes a day.

So in carpool line, when I take my kids to school or pick them up, I just

fire off a couple of emails or call them or whatever.

So that was that theory.

The compliment congratulated consoling is really just kind of three things that

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 going to pass away.

Like your life's going to change, man.

If you have someone that's grieving and you don't reach out to them,

they will never forget it.

They'll never, oh, you can't human nature.

You can't even help but take inventory.

Who reached out and who did?

You're just aware.

I just lost my father.

I know everybody that called me.

I know everybody that didn't call me.

And the people that didn't call me don't get a pass.

They don't get a pass.

So you always want to console the people that

you know, something happens to a friend in your life.

That's great.

You want to congratulate them, you know, and then you want to compliment,

you know, show them and say, listen, you guys have an amazing podcast.

You did it yourself.

You know, you guys decided to like sold some businesses and here you are,

you know, bringing on inspiring people to inspire entrepreneurs all over the world.

And I just want to congratulate you on your success, man.

I'm, you know, you just call someone out of nowhere.

You default to calls or texts.

Either way, I just think I personally like handwritten letters.

Here's one, um, because I feel like the intent.

It takes a little longer, but to actually get a stamp, lick it, go to

the mailbox, put it in the mailbox.

It's received completely different than just sent.

But, you know, so by like in the pecking order, but you don't have

the ability to do that, it takes too long.

But at the end of the year, I do like to write 25 to 50 handwritten

thank you letters every year.

I have a whole close out the year process that I kind of teach people,

but like, and that's one of, you know, but you compliment, you

graduate in a good soul and you do that to people.

And like, if I, Sam, if I hit you up, God forbid you had something bad.

And, and, and I don't even know, I just met you for the first time.

Other than the question about how my borough rate, I love you.

So if I, if I would have all you up after one meeting and say, Sam, man,

I heard about XYZ, man, I'm so sorry that happened to you.

And then four months later, I'd call you up and say, Sam, man, you guys

just hit five million downloads a day.

Congratulations, man.

And then I call you up again at the end of the year and say, Sam, I

just want to let you know, man, then question you asked me about, about

my burry, you know, I would rethought it and I want to compliment you

because you asked the tough questions.

And you know what, that's the seat that you're in.

And I give you credit for asking questions like that to people on the

other end, and I really admire you for that.

I do those three things in that year.

You're going to think differently about.

Oh, you'll be his hero.

He'll be all of our heroes, to be honest with you.

That'd be incredible.

All right.

Well, dad.

Sean, you laugh about that.

We're laughing about it.

But let me ask you a question.

Who does want to be a hero?

You're right.

Who doesn't want to be a hero?

We like, if you tell me, I don't have to run into a building and save,

save someone.

I can just do that.

And I could be a quote unquote hero.

Like, you know what, I build my career doing that.

Well, so this is about relationship.

You also have others about skill building, life experiences, explain

some of your other kind of life rules.

Cause I think these are really worth sharing.

You know, people I think will be entertained and inspired by the business

stories, but my hope is that that actually was just buying the right to

drop a little wisdom on them at the end here.

Cause this is the stuff I've liked the most from you, from your story.

So, so tell, talk about, you know, the sort of misogy or the, the Kevin's rule.

Like these are pretty foundational.

Yeah.

Well, that goes into kind of the planning that I showed you on the calendar.

And I really have to do two or three things every year at the beginning of the

year.

This is actually perfect timing.

I don't know when this is going to air, but like November, December, when you

look into 2024 or the next year.

I try to have one big year defining thing on my calendar every year.

Last year was my bike ride across America.

2015 was living with the seal.

The book I wrote 2017.

I lived on a monastery 2016 or something.

I started 29 or 29 in this company with my partner.

So there's an old Japanese ritual called the misogy.

And we took the liberty to kind of create our own version of what that means.

But basically it means that every year you do one or the way I've interpreted it.

Is you do one big year defining thing.

And you should have something to show for it every year.

By the way, if you're 35 years old, I don't, 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, spend a couple of hours learning something I didn't know.

Um, I coined it Kevin's rule because Kevin and I were camping him out

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, what do you mean?

He's like, so at the end of the year, I got six mini adventures.

If you're 35 and you live to be 55 and you have six mini adventures, that's 300

mini adventures and 30, 50, I'm sorry, 50 year defining things.

You're a misogi and 300 mini adventures.

Sean, I don't care how much money you have or how little money you have.

At the end of your run, if I go to you and you're 85 years old on your 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.

It's a two percent. Is that two percent? Six percent?

What is that? We have a rule here. We don't do public math.

So don't worry, you're off the hook.

OK, there we go.

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

Have you ever hung out with Rob Deirdeck?

You guys are really similar.

We had him on and I think I've said publicly, he's one of my favorite people.

And you have this similar quality where you just have a framework

and you know what you like and you stick to it and you're really intentional.

And I appreciate that on your terms,

which is what I think the highest calling thing we respect on the pod is

somebody who defines their own terms and then lives on them,

even if you don't even if somebody is successful, people don't do that.

Like even people who are wealthy, they're like, I fucking hate my life

because I'm tied to this job that I actually don't like doing.

And you're a great example.

Your your your definition tends to be exciting and awesome

because you're doing all these adventures,

but it doesn't matter what your your definition of of like your framework is.

You've done a cool job of defining it and sticking with it.

And I appreciate that.

Well, one cool thing that's different is Rob's is all about maximizing.

He's like efficiency. How much?

How do I use my time? How do I allocate it?

And how do I get the most done in that time?

Whereas I feel like Jesse's almost like it's a different relationship with time.

It's like, how do I have the maximum number of of incredible experiences

and amazing relationships and moments,

whether that moment took five seconds or, you know, five days or five weeks?

It doesn't really matter.

It's like maximizing kind of like squeezing the juice out of out of the fruit,

you know, versus versus, you know, trying to optimize every moment

in a generation of hustle and grind, which is so obvious.

No shit. You got to work hard.

That message gets lost and you don't want to give up your twenties

in your thirties and your forties and certainly not your fifties.

If you can avoid it, just grinding and chasing something

that you can get the same feeling doing something else.

Well, we feel lucky for having having you on 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, 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, you know, maybe something,

maybe something more wise will come take its place, but that's it.

And that's the pod.

Machine-generated transcript that may contain inaccuracies.