Founders: #323 Jimmy Buffett

I think you're gonna like this episode. I did a ton of prep and research. I read over 700 pages,

read a bunch of articles on all his different business holdings, and then I also watched this

documentary where he was interviewed for about an hour over 20 years ago. And he said something in

that documentary that I thought was fascinating. He also mentions it in one of the biographies as

well. And he talked about the more serious he got in his career, the older he got, the more

serious he took in the practice of his craft and the service that he was providing to his customers.

The more important his sleep became. And Jimmy had a great line where he's like,

I wake up now at the time I used to go to bed. And Jimmy's not alone in that realization that,

hey, the quality of your sleep is tied to the quality decisions you make and the quality of

the product and the service that you're putting out. And so therefore you should try to do everything

you can to optimize and make sure that you're getting the best rest possible. And the only thing

that I have found that has actually improved my sleep has been an eight sleep. I have never had

the ability before to change the temperature of my bed before I had an eight sleep. I had no idea

how that one thing would actually improve the quality of my sleep. I like to keep my eight

sleep ice cold and I make sure that it's cold before I get into bed so I can fall asleep faster

and I wake up less during the night. I truly believe that feature alone is worth 10 times

the price. Eight sleep is so good that now every time I travel, you know the product's good is

because you notice its absence. It's to the point now when I know if I have to travel, I'm like,

oh my goodness, I'm not gonna have my eight sleep. And that realization is spreading. I've heard from

a bunch of people, listen to founders that bought their eight sleep and love it, but it's also

spreading in my own household. My daughter was feeling down and she wanted to sleep in bed with

her mom and so I gave her my side of obviously the bed and I was like, hey, do you want me to keep

the eight sleep on or do you want me to turn it off? So no, please keep it on. So the next morning

I asked her, I was like, what'd you think? She says, I love it. Can I have one? And so I told her

it's a good thing. I know how to get $150 off. I believe there's very few no brainer investments

in life and I do believe eight sleep is one of them. If you want to try an eight sleep and get

your own, you can get $150 off by going to eightsleep.com forward slash founders again,

to get $150 off and get the best sleep of your life, go to eightsleep.com forward slash founders.

And speaking of travel and noticing a product's absence, I'm actually traveling to New York City

in less than two weeks. There's only two weeks left before I'm doing this live show in New York

City. I'm doing with Patrick Christianity from the invest like the best podcast. It is on October

19. There is less than 100 tickets left available. I'm excited to do my first ever live show.

I will be missing my eight sleep mattress because obviously we sleep in a hotel in New York City.

However, if you have not gotten your tickets yet, I will leave a link down below. And you can also

go to founders podcast.com to get tickets. And you can go directly to the venues website, which is

Webster Hall in New York City. This is gonna be a one time only show. So make sure you don't miss

it before you go. Do me a favor. Patrick just invited me to be interviewed on his excellent

podcast. I did it a few weeks ago. I will leave a link down below. But if not, you can just search

in your podcast player, whatever you're listening to this on and search for invest like the best.

Look for episode 343 David Senra in the service of founders. I really enjoyed that conversation.

And really any conversation I get to have with Patrick, it's 90 minutes, I think there's a lot

of useful information. One other thing before we jump into this incredible world and life,

the Jimmy Buffett stories got me super inspired. It got me fired up. I spent an unbelievable amount

of time just living in this guy's mind in his world, what he was able to build over such a long

period of time. I found very, very inspiring. But I do want to tell you about one other product

that several of my founder friends are also using and that is Vesto, Vesto with a V. You can check

them out at Vesto.com. So that's V as in Victor, E as an egg, S as in Senra, T as in Tom, O as in Oprah.

And Vesto's mission is to make it easy for you to invest your business's idle cash. What Vesto

does is help businesses of all size invest their cash in US treasuries. When you do that,

when your business owns treasury, that cash is backed by the US government and it earns interest

while it sits there. I have one founder friend who raised a bunch of venture capital money.

And so he uses Vesto as a way to extend his runway. And I have another founder friend who

bootstrapped his company and he uses Vesto to get a better rate of return than if that cash

was just sitting in his bank account. If this sounds interesting to you, I highly recommend

that you go to Vesto.com. Remember Vesto with a V, V as in Victor, E S T O.com. And check out what

they have to offer. I know the founder Ben actually just saw him again. I've spent a bunch of time

with him, but I should just saw him again. I had dinner with him last week. If you schedule a demo.

So if you go to Vesto.com and you schedule a demo, you actually speak directly to the founder

Ben. I think he's very impressive. I think if you speak to him, you'll be impressed as well.

Make sure when you speak to him that you tell him that David from founders

sent you. And with that, let's get into the life of Jimmy Buffett and the world that he created.

I made it through adolescence without killing myself in a car. I flunked out of college.

I learned to play the guitar. I lived on the beach, lived in the French quarter,

finally got laid and didn't go to Vietnam. I got back into school, started a band,

got a job on Bourbon Street, graduated from college, broke up my band and went out on the road

solo. I signed a record deal, got married, moved to Nashville, had my guitar stolen,

bought a Mercedes, worked at Billboard magazine, put out my first album and went broke.

Wrecked the Mercedes, got divorced and moved to Key West. I sang and worked on a fishing boat,

went totally crazy, did a lot of dope, met the right girl, made another record, had a hit,

bought a boat and sailed away to the Caribbean. I started another band, worked the road, had my

second and last hit, bought a house in Aspen, started spending summers in New England, got married,

broke my leg three times in one year, had a baby girl, made more records, bought a bigger boat and

sailed away to St. Bart's. I got separated from the girl, sold the boat, sold the house in Aspen,

moved back to Key West, worked the road and made more records. I rented an apartment in Paris,

went to Brazil for Carnival, learned to fly, went into therapy, quit doing dope, bought my first

seaplane, flew all over the Caribbean, almost got a second divorce, moved to Malibu for more therapy

and got back with the right girl. I worked the road, moved back to Nashville, took off in an F14

from an aircraft carrier, bought a summer home on Long Island and had another baby girl. I found

the perfect seaplane and moved back to Florida. My son joined me in the house of women. I built a

home on Long Island, crashed the perfect seaplane in Nantucket, lived through it thanks to Navy

Training, tried to slow down a little, woke up one morning and I was looking at 50, trying to figure

out what comes next. That was an excerpt from Jimmy Buffett's autobiography, A Pirate Looks at 50.

That is not the book that I'm going to talk to you about today, although I did read it to prepare

for this podcast. 99% of the stuff I'm going to talk to you about today actually comes from a

biography of Jimmy Buffett called Jimmy Buffett, A Good Life All the Way and that book was written

by Ryan White in the subtitle, A Good Life All the Way is actually a quote from Jimmy Buffett

when he was older describing his life up until that point. And so Jimmy passed away a few weeks

ago and I think now is the perfect time to do an episode on his amazing life and career. There's a

great line later on in the book when they were talking about the fact, you know, Jimmy wasn't

a mainstream artist, didn't have a ton of like top, you know, top 10 or top 100 hits. And somebody

said if you looked at his career compared to other people that had similar like a similar record,

he should be going on and performing at 3pm in the middle of a state fair. And yet that is not at

all the outcome that he had. Jimmy had a 50 year career. He built a billion dollar fortune. He made

personally 30 to 70 million dollars a year. He was respected by his peers, loved by his family

and had millions of fans. So the biography I'm holding in my hand tells the story of how that

happened. Before I get into this book, I want to read one more passage from his autobiography,

which I absolutely loved. And he was asked, what are you going to do with your life? And this was

his answer. Live a pretty interesting one. I have been called a lot of things in these 50 years on

earth. But the thing I believe I am the most is lucky. I have always looked at life as a voyage,

mostly wonderful, sometimes frightening. In my family and friends, I have discovered treasure

more valuable than gold. I have seen and done things that I read about as a kid. I have dodged

many storms and bounced across the bottom on occasion. But so far, lady luck and the stars by

which I steer have kept me off the rocks. I have paid attention when I had to, and I've made more

right decisions than wrong ones to end up at this moment with 1000 ports of call behind me. And I

hope 1000 more to see my voyage was never a well conceived plan. Nor will it ever be. I have made

it up as I went along. So I want to start with his father. He has he's going to have a rather

tumultuous relationship with his dad. They actually are estranged for quite a while. And I think

Jimmy wasn't in wasn't until Jimmy was in his 30s that he actually reconciled with his father.

And I think you could trace Jimmy's desire to live an interesting life and to have treat life

like an adventure to his grandfather because that's exactly what his grandfather did.

Jimmy Buffett wasn't the first Buffett to set out for adventure. That would have been his

grandfather, the former sea captain. His grandfather ran oil and ammunition to Europe during World

War One. He had hustled oil to Japan for the Standard Oil Company. And he had been a seal hunter

in the Indian Ocean. His grandfather spent a lot of his life exploring the world by sea.

Jimmy would do some of that later in life as well. It said life would loosen up when his grandfather

was gone and tidy up when he returned. He was the moon controlling the tides to his grandkids.

He was the key to the universe. Everybody around Jimmy lived a conventional existence

besides his grandfather. And his grandfather changes the course of his life, not only by

his example, but in one of these conversations. So it says on one day, the captain pulled out

a nautical chart and led his grandson to the pier. Where are we? He said. Jimmy responded.

Jimmy's a little kid when this is happening. We're on the crab pier. Look again, the captain said,

pointing to the chart. Slowly his point came into focus. They were at the beginning of everything.

From where they stood, from that point, the only thing standing between Jimmy and the world

would be a lack of imagination or an overabundance of caution. At the bottom of the map,

Captain Buffett had written two words, start here. All he had to do was leap and the world would be

his. And this is such an important point to think about because the captain is giving the advice

to his grandson, the advice that he took himself in his life. He was born in Nova Scotia. He came

from a long line of coal miners. He was expected to be a coal miner when he was younger. Instead,

he jumped out of a window, ran away and chased after a life on the sea. And so much later in life,

Jimmy had reconciled with his father, his father's Alzheimer's, and they go back to Nova Scotia

shortly before he dies. And they just want to see where their whole family started.

And I think what Jimmy's father says here about his own father, Jimmy's grandfather,

is very important to think about how the decisions that you and I make today can resonate

through the generations. And so Jimmy's asking his dad, what did you think of this day? We went

and saw where the captain had grown up, where his family was from. And his dad said, well,

I'm just glad that he jumped out that window or we would have all been goddamn coal miners.

And so when I read that, I thought of the powerful effect that the decisions of Captain

Buffett had on not only his son, but his grandson. But I also thought it was interesting because now

Jimmy's dad is a much older man. He sees that his son is very successful. The source of conflict

in their relationship, in that father-son relationship, was the fact that Jimmy's dad

lived a conventional existence. He wanted his son to do the same. And Jimmy Rebelle,

he's like, no, I don't, I want a life full of adventure. So he runs away and decides,

hey, I want to be a musician. I am willing to take a risk. I will play on street corners for

tips, which he does for a long time. So I want to jump into the late 1960s. Jimmy is in his early

to mid-20s. And what is fascinating is when you read a lot of these biographies, you realize that

there is some sort of innate talent that is usually revealed early. So nobody knows who Jimmy

Buffett is now, doesn't have a record deal, is playing in bars and pizza joints and on the street.

But he's starting to, at this time, the center of the music universe, especially for the music

that he thought he was going to play, was in Nashville. And so he's going to these meetings

and people would notice the same thing. They said, the first thing I noticed when Jimmy walked in

the room was that persona, the Jimmy persona. He wasn't yet the Caribbean cowboy, but he had a

glow. There was a presence to him. Remember that point for later, because it's really important

to understanding the success that Jimmy has later in life. You could think of him as a musician.

Really, what I think of him as is a performer and an entrepreneur. And I think that'll be obvious

by the time we get to the end of this story. But I think it's important to stop and really think

about the risk he was taking. He said, like, once he discovered his guitar, there's no way that he

was going to have a conventional existence. He actually talks about that multiple times, like,

I had to go in an opposite direction. I wanted to be a Bohemian. I wanted to be free. I wanted

to be unfettered. In fact, one of his heroes is Mark Twain. There's a lot of Mark Twain in Jimmy

Buffett. Yeah, this was top of mind, because I just did an episode on Mark Twain. That was episode

312 if you haven't listened to it. But the other person that young Jimmy Buffett reminded me of

is actually, surprisingly, Arnold Schwarzenegger has this great line in his biography, the one,

the biography that he wrote when he was in his 70s, called Total Recall. And in that book,

he says, there was nothing normal about me. My drive was not normal. My vision of where I wanted

to go in life was not normal. The whole idea of a conventional existence was like kryptonite to me.

That line especially, the whole idea of a conventional existence was like kryptonite to me,

applies to Jimmy Buffett as well. And so to try to make it as a musician,

Buffett starts to give himself a different kind of education. He's willing to

perform anywhere that will take him. He performs in pizza joints. He performs on street corners.

He'll perform in bars. And so it says, New Orleans was school. He studied the way musicians

worked the crowds. He would set up on street corners and work for tips. And so this is a

great description of what's happening. Buffett was smart enough to see a street corner and a bourbon

street bar as but another departure point with as much potential as the old crab pier. Start there.

And so it's by taking every single job that's offered to him that he actually gets his first

permanent gig. He gets a permanent gig at a bar in the corner of a hotel. That bar is called the

Admiral's Corner. This is very important because you can think about the life and career of Jimmy

Buffett, just like you could think of the life and career of his good friend Warren Buffett.

Their lives are illustrations in the power of compounding. And so this is the first time in

his career that he's able to stay in one spot and start developing a dedicated audience, start small.

Every day gets a little bigger and a little bigger and a little bigger. Remember, there's 50 years

ahead of Buffett. Most of his success and most of his money is going to be made 30, 35 years from

now, just like if you ever look at the net worth of Warren Buffett by age, something like 99% of

it or something like that comes after the age of 50. And so while he's working on his permanent

gig, he's also going back and forth to Nashville to try to get a record deal, try to make as much

music as possible, try to become known. Nashville is the center of what he believes at this time

is the center of the music world. It's where he has to be if he's going to succeed. He's going

to accidentally realize that's not the case because he doesn't succeed at all in Nashville.

And he flees to Key West and that's where he finds his sound. He really defines his own genre

and becomes in turn completely differentiated from anything else that was around. We're not

there yet. He's in Nashville. He has to get a real job at Billboard magazine because he can't

pay his bills. The side effect of this job though is not just a paycheck. It helps him build a lot

of relationships inside the music industry and it helps him school him to the game at the exact

same time. So he says I had to get a real job. Billboard magazine said they needed a writer.

So Buffett starts covering the news like every day. Some there's a new artist that's being

broken in Nashville. He writes about them. He will also write music reviews of albums and shows

and things like that. But the most important thing this job did was that it opened a number

of doors. He went into meeting people, the music executives, who has people working at the studios.

He winds up meeting people that work at publishing houses. He winds up developing

friendships with people that work at Billboard that actually teach him the music business.

One guy was Bill Williams. Bill Williams was the editor of Billboard's Nashville headquarters

and this is what he taught Buffett. He knew the town and the business that turned its gears.

A hit song was nice but owning the publishing on a hit song was even better. So they would hang

out. They would drink at the end of the day and Bill is just sitting there schooling a young

Jimmy Buffett to the game. And so this is the first time in the book that this is mentioned

but it's mentioned over and over again. It's the fact that artists are a disposable commodity.

There's always another kid coming to town who can sing. You've got to handle the business end

of the music business. You cannot think of yourself as just an artist, as just a musician.

You will get taken advantage of. Talks about, you know, yeah, you have a hit song but the guy

that owned the publishing is making all the money. And Buffett is going to take these lessons and put

them to use. Maybe better than almost any other musician in history. Like there's been what,

hundreds, maybe tens of thousands of musicians. How many of them are billionaires?

How many of them built businesses bigger than their music? You're talking what, 10, 15,

the number is less than 20. And Buffett is one of them. And when I'm reading this part,

this part reminded me, I did an episode on Jay-Z's autobiography, which is absolutely

excellent. The book is absolutely excellent. It's episode 238 if you haven't listened to it.

But there's a time where Jay-Z's in his early 20s. This is reminding me of the lesson that

Buffett, that Jimmy Buffett is getting in his early 20s. Jay-Z's in his early 20s when he reads

this book called The Hitman. And The Hitman is essentially a history of the music industry

about how artists get taken advantage of by executives and the people that actually control

and own all the valuable assets. And so Jay-Z in his 20s is just like Jimmy Buffett in his 20s,

was like, okay, I'm going to learn this and I'm going to make sure that doesn't happen to me.

And the interesting thing is, if you fast forward 30 or 40 years into both of their careers,

they both apply these lessons to the point where they both built multiple billion dollar fortunes.

Where their stories depart is Jay-Z's first album was a success. Reasonable doubt is still

considered a classic to this day. Jimmy Buffett had a decade and a half, two decades of struggle.

So he's in Nashville. He gets his first record deal. He's putting out songs. He's putting out

music. Nobody is knocking on the door. Nashville is not interested in Jimmy Buffett's sound.

And so you'll see a bunch of sentences spread out through the book describing this time in his

life. And I'll say something like, the album didn't do anything. Nothing happened. He was

completely stiffed. Jimmy Buffett got turned down by every single label. And the bad times

were not just in his career. He got married young. It was a very hard time. They were young.

It was very hard on them because they had no money and nothing was going well. And so he winds

up at the same time he's failing professionally, right? He winds up getting divorced. And so it's

just year after year of struggle and rejection. So he's like, all right, I got to get out of here.

He said he hated Nashville. And he's like, I need a change of place. I think I need a change of place.

And so he goes, where can I go? He goes to the furthest place he can think of. And he goes to

Key West. And so there's two things that came to my mind when I was reading this part of the story.

The first thing that came to my mind was that excellent, excellent quote by Steve Jobs. He says,

you cannot connect the dots looking forward. You can only connect them looking backwards in life.

So you have to trust that the dots will somehow connect in your future. You have to trust in

something. And the thing that Jimmy is trusting in is himself, his instincts, his intuition. He

does not yet know this is going to be the most important decision he ever makes because he's

the first person that is able to actually package up and sell this Key West lifestyle.

The second thing that came to mind is this maxim that has been on my mind a lot and that is obvious

in hindsight now that I've read 330 or however many books I'm on. When it comes to the life of

an entrepreneur, your experience is likely to be very similar to Jimmy Buffett's experience up

until this point where everybody's saying, Jimmy, we don't like what you're doing. There's no market

for that. We're not going to sign you. We're not going to help you in any way. And so the maximum

is is that you should believe that your opinion on what you're working on, right?

Your opinion is greater than the opinion of everybody else around you.

Jimmy Buffett believed in himself and his music and I'm going to use the parallel that keeps

popping up my mind as well. Jay-Z did too. Everybody else would not sign Jay-Z. He went to

other record labels. They wouldn't sign him. You know what he did instead? He started his own.

His first album is on a record label that he founded. That is him telling you by his actions,

my opinion of what I'm doing is more important and is greater than the opinions of every single

other person that turned me down. The decision that Jimmy makes here is not obvious. It's it

may be obvious in hindsight that I'm going to describe what Key West was like in the 70s when

he's there. Key West was and is for dreamers, schemers and contradictions. It is hot and the

heat breeds its own sweet lunacy. He's like in a city or a town of misfits. There's writers,

there's artists, there's outcasts, everybody's doing drugs. There's a bunch of people down there

during this time and before and after. Buffett goes down there, rents an apartment for $150 a

month. At this point in Key West, now if you wanted something oceanfront Key West, you're

paying millions of dollars, he was paying $150 a month for $150 or $200 a month, you could actually

get an apartment on the ocean. This is a different Key West than what it's like today.

And then what does he do? He goes to the local bar and he's like, Hey, can I just play for your

customers and you could pay me in tips and alcohol? And they say, yes, this book is full of stories.

These are wild men in a wild place during wild times. So the bar he's playing at, it's like the

bar everybody goes to. Now this is the kind of place that Key West is. Think about the city that

you live in, right? This is what the city that he's living at a time. Key West was run out of that

bar in those days. The mayor was there, the police chief was there, the fire chief, the city attorney

and the state attorney. You could get arrested, bonded, tried and get a building permit all in

the bar. This is the beginning of this party lifestyle that Jimmy packages up and sells.

He sells like a more moderate version of this. I mean, there's insane stories about this,

like this guy's walking around the bar. He has an aspirin bottle. He took out all the pills

and filled it up with cocaine and put a straw on it. There's a line later on describing all the

citizens of Key West at the time. They said they were dedicated to two pursuits, inebriation and

fornication. There's a story in the book where somebody spikes all the alcohol with LSD. So

everybody's drunk and then tripping on acid. And so at the end of the night, one of Jimmy Buffett's

friends goes out to the sheriff's car and the sheriff hands the keys to Jimmy's friend and says,

hey, you have to drive. He's like, why am I, we're both like drunk and high on acid. Why am I driving?

He's like, well, because I can get you out of trouble, but you can't get me out of trouble.

And at the end of the story, there's a great line. It says, if you want to know what Key West was

like back then, there you go. And so Key West at this time is the opposite of Nashville. It's

isolated. It's cut off. It's the last place on earth you're going to move to if you want to make it

as a Southern or maybe country musician. But it's because of the decision and in part because of

the isolation that makes Jimmy so valuable. Jimmy understood at a very young age that you should

not try to be the best. You should try to be the only. Jimmy stood out in Key West in a way that

he would not have in a big city. Had he left Nashville for New York or Los Angeles, he would

have been just another folk singer. But Key West didn't have a Jimmy Buffett and Key West gave

Buffett a canvas that no other songwriter had. And so one of the main criticisms of Jimmy Buffett

at the early stages of his career, and really people didn't stop saying it for two decades into

his career, to then people realize, oh my God, he's got this massive following, is the fact that

what are you? You have no genre. You're not a folk singer. You're not doing rock and roll.

You're not doing country. Decades before Peter Till said in zero to one that if you want to create

and capture lasting value, don't build an undifferentiated commodity business. Jimmy was

doing that through his actions, through his instincts, through his intuition. He was very

self aware. And so what's happening now is he's building up this small but loyal following in

Key West, and he's still taking every single job he can get anywhere in the country. And so the note

I left myself was as I'm going over the sections, like, oh, this guy's got infinite runway. So what

do I mean by that? In addition to reading two books to get ready for this podcast, I watched a

documentary, took notes on the documentary, read a ton of articles trying to figure out because

this guy's got a massive business. They did $2.2 billion in sales in 2022. That doesn't include

hundreds of other licensing agreements. It doesn't include his $400 million alcohol business.

This guy built a money printing machine, but it didn't start like that. He says, like, when he

started getting paid, when he was back in New Orleans, he was getting paid $150 a week as a

headliner in a bar. And he's like, that's it. I'm at the top of show business. There is nothing

better than this. And so he's living in a hundred, now he's in Key West, he's living in $150 a month

apartment, doesn't have to spend a lot of money. And because his costs are so low and he's happy,

he's just like, listen, I just don't want a conventional existence. I just want to play

music and I want to entertain people. He's now got infinite runway. And so his costs are low,

he's got infinite runway. And now he could just, all he's dedicated to is practice, practice,

practice. That's another main theme of this book. Buffett, Jimmy Buffett wanted reps, reps,

reps, reps. He understood that's how you get good at anything. And so when he's not in Key West,

he's in Atlanta, he's in Chicago, he's in New Orleans, he's in Biloxi, he's playing colleges,

he's playing bars, he's traveling all over Texas, he's playing Dallas, Houston, Austin,

to get to these gigs, he was willing to drive, take a train or fly. And here's a great line in

there, he needed to play live, he needed to hit the road, he needed to perform. There's no substitute

for experience and there's only one way to get it. And he's running his entire business out of the

bar in Key West, he doesn't have a phone. So this guy that's booking them said, this is a time before

fax machines, this is before email. Buffett didn't even have a phone of his own. So the guy that's

booking him would call the chart room, which is the bar that he's working on. And he says,

that's where we did business, I'd leave word for Buffett to call me back from there.

Jimmy had a fierce work ethic, he had a fierce work ethic when he was in his 20s, he had a fierce

work ethic when he was in his 60s and his 70s. He talked about the documentary, he was interviewed

for the documentaries, he said, yeah, I'm definitely a workaholic. And so one thing that

he's working on at this time, the way to get successful, there was a path right in the music

business to get successful. That path was through radio, radio refuses to play, Jimmy's trying to

get on the radio over and over again, they refuse to play him. And radio is what's influencing

record executives, they influence not only what people listen to, so the consumers,

but also the executives in the music industry. This is really important. It says radio was

what record executives knew to establish an artist to build a fan base and sell records,

you had to get airplay. Different was a risk, risk was a hard sell. Buffett wasn't like any

other artists at the time. And so along the way, there's a bunch of people that meet Jimmy

and have a fear, there'd be individuals, multiple individuals that had a deep belief

that he was going to be successful. There's one guy that's trying to help him at this point,

this guy named Don Light, and he's describing what's taking place and why Jimmy, even though he's

starting to build a following on the road, why can't he get any radio play? Why can't record

executives, like why don't they want to sign them? Why don't they want to put resources behind them?

And so he says, record labels look to the past and what had worked. Light was pretty sure that he

was watching the future take shape. Kids were sitting in front of Buffett, meaning the crowd,

in increasing numbers. The receipts from these concerts were adding up. And so Light's point

was, if you were a record executive, right, he says they weren't off base on that, that Jimmy

was different, Jimmy was new, and that that new and different is a risk and a hard sell. So they

weren't off base, but they were wrong, just the same. This is such an important part of the story.

In that documentary, Jimmy was talking about this time in his life, he goes, it is ironic

that it was never categorizable. That's what they would tell him. It is ironic that it was

never categorizable. And now I'm a category. I wasn't categorizable. Now I'm a category.

The idea behind that statement is why he was able to build such a valuable business.

And so when I got to this part of the story, made me think of Bob Dylan's autobiography

that I did all the way back on episode 259, because Bob was talking about this. And he was talking

about the people were asking him because his sound was just so different and so odd. And so he says,

hey, he was asked like, who do you see yourself like in today's music scene? And this is what

Bob Dylan said before he was famous, before he was successful. I told him nobody, I really didn't

see myself like anybody. What really set me apart in those days was my repertoire. It was more

formidable than the rest of the players. There were a lot better musicians around, but there wasn't

anybody close in nature to what I was doing. Don't try to be the best try to be the only in that

documentary. Jimmy's very self aware. He says, listen, I'm an adequate musician, and I'm a fair

singer, but he's a great performer and a world class entrepreneur. And those kind of people

cannot work within a system they have to create their own. Here's a great line on why Nashville

was not right for Jimmy Buffett and why every time he went there, he got rejected. No one's ever

eager to fix a cash machine that isn't broken. Go back to episode 300, James Dyson, still my

favorite book against the odds and autobiography by James Dyson is still my favorite book out of

every single book that I have ever read for this podcast. What was James' mistake? Oh, great, James.

You invented the world's first cyclonic vacuum. Who did you try to sell to? You try to sell to a

company that made $500 million a year selling vacuum bags. You eliminated the bags. Of course,

they're not going to buy it because no one's ever eager to fix a cash machine that isn't broken.

And so James, just like Jimmy, had to find their own way in. And the way you find your own way in

is you do it yourself. This metaphor I'm about to read to you, this metaphor is a is the way to

think about Jimmy and his approach to his career. It is written about a poet and a painter named

Kenneth Patchen. I am going to read it to you taking out Kenneth's words or Kenneth's name

and putting in Jimmy's and it's perfect. It fits perfectly. So this is my version of the story that

I think will illustrate the point I'm trying to make to you. Buffett was accomplished, if not

exactly appreciated. Many critics found Buffett naive and romantic. Even the most generous praise

was usually grudgingly, as if Buffett had somehow won his place through sheer wrongheaded

persistence. Sure of who he was and what he was doing, he kept at the job of being Jimmy Buffett

until people came around or didn't. He didn't worry about it. And so what is Jimmy's response to

being told no by the industry, being told no, you're not categorizable, we're not putting

any marketing dollars around you, we're not putting on the radio. Well, his response to this

sounds a lot like if you listen to the episode 314, Paul Graham, how to do great work. I love this.

Paul Graham says something that grows exponentially can become so valuable that it is worth making

an extraordinary effort to get it started. The Jimmy Buffett version of that idea sounds like this.

He made up his songs when nobody was looking and played them for anyone who would listen

in coffee shops, student unions and listening rooms. And so even when he was a young man,

he had this relentless self belief in himself and his work. And he was trying to make a product

that only Jimmy Buffett could make. And so he releases this album. And so he has a song in

there called Why Don't We Get Drunk? This is his first, what we would call like a hit,

like a middling hit, but at this time it was the biggest song they ever had. And what was fascinating

is people around him were trying to change the lyrics of the song, because why don't we get drunk,

if you leave it there, that's gonna, that'll play on country radio. Nashville will play that.

But he adds in the lyrics, it's why don't we get drunk and screw. Remember, Jimmy is living in

Key West, they are dedicated to the twin gods of inebriation and fornication. And so he's writing

his lyrics about how he's living his life at this time. And so people around him say, hey,

you got to take those words out of there. This could destroy your career. And Buffett said,

why I don't even have a career yet. How can it destroy it? This could make it. And so the entire

album, it's called a white sport coat and a pink crustacean is like that. And this is what it says,

this album was the first Jimmy Buffett record that only Jimmy Buffett could make. It wasn't folk

or country or rock. And it wasn't trying to satisfy anyone but Jimmy Buffett. And so Jimmy is

working with Don Light, they share the same philosophy. And the philosophy is that anything

that rises above the mire is a success. Anything that draws attention to itself and continues on

without some sort of great preposterous hype cycle involved is a success. And that's what Jimmy's

music started doing. There was no niche, there was no genre that you could put them in. In fact,

he created his own genre. It's called Trop Rock, Tropical Rock. And so Jimmy just keeps on doing

what he was doing. He tries to get as many reps as possible. He winds up making like eight or nine

albums like in the first like 10 years of his career. I think he winds up publishing over like

30 albums in his lifetime. So he grabs his guitar and he goes back on the road and will play literally

any any place that will have him. And then he starts doing something that is very fascinating.

And they talk about this in documentaries, you can see it on YouTube as well. He doesn't just

play songs. He will play a song and then he'll just talk directly to the audience. Sometimes

he'll talk for 12 minutes and then play another song, then he'll play a few songs, then he might

talk for 20 or 30 minutes. This guy's like a, again, think of him more as a performer, not a

musician. And what you realize is like, wait a minute, these people aren't there just for the music,

they're there for him. And this idea that Jimmy was just communicating directly to his audience is

really important because it's repeated over and over again, says stuff like, hey, this guy could

talk and people loved him for it. He was quick. Another description on stage, Buffett was part

Barstool philosopher and everybody's stoned best friend. He was a run on sentence punctuated by an

occasional song and he was busy. He would find himself far away from Key West for longer periods

of time. Buffett had on stage wanderings and extended monologues, people like those, they paid

to hear him talk as much as sing. Again, they're not just buying music there, there for him and

anything that he does. He had no idea it's going to take like 15 years, maybe 10 or 15 years from

around the story. So he actually turns that into a business and that's what allows him. The business

supports the music. If he just did music, he would have never been able to survive. He just doesn't

know that yet. Now this is hilarious. So that song, that first hit, right? Why don't we get drunk?

It winds up being a massive hit inside of bars. So a huge revenue stream of bars at this time

were jukeboxes, right? You go up, you pay 50 cents a dollar, you get to choose what everybody else

in the bar is listening to. So he winds up, and I didn't even know this was an entire industry

and they actually tracked how many sales. So in 1973, he sold on jukeboxes 50,000 copies of that

song. Why don't we get drunk? And so he's like, Oh my God, I'm going to be rich. I'm going to take

this money from the song and I'm going to buy a boat. And the reason that didn't happen is because

at this time, the mafia controlled the jukeboxes and they would never pay out a dime. A young

Jimmy Buffett gets stiffed by the mafia. This is also a lesson he learns later on. Okay, I need to

control my own distribution. And so what is Jimmy's response to the fact that he's got a song that

a lot of people are requesting, a lot of people are playing? Well, it says, there'd be no slowing

down. Jimmy Buffett played a concert at noon on a Monday in a student union center on the campus

of Purdue. The admission was free. That is not a gig you play for fame. You play because it's your

job. He would play any gig anywhere that would have him. And so at this point, that is repeated

over and over again. This is the note I left myself on this page describing Jimmy blue collar work

ethic, learning machine loves it won't quit. Again, people that have a blue collar work ethic,

learning machines love what they do and won't quit are so hard to beat. And so now that he's been at

it for almost a decade, we start to see the very beginning of this compounding of his customer base.

And it's read the word of mouth again, he's not going to sell music, he's going to sell live music,

and that is a much more durable business. So it says the audience was singing words to every song,

and they didn't hear those songs on the radio. They knew those songs because maybe they bought a

record or a friend had bought a record and then it played it for them. They knew those songs because

they caught a show, then caught Buffett again, the next time he was in town and brought more friends.

This will be the key to everything else that comes after. Okay, so years ago, I used to read

this blog all the time called priceonomics, and I like they would repackage their blog posts into

books. And I remember one thing I didn't know I'd never heard of this, this group called the fish,

and I was shocked at how much money they were making. And so I want to read from this blog post

called the business of fish. And so fish is mentioned in the book, there's actually a lot

similarities in between the way they built their business and the way Jimmy built his business.

And so this article is several years old. But it says over the past four years, the rock band

fish has generated over $120 million in ticket sales. They are one of the most lucrative touring

acts in America and have generated well over a quarter billion dollars. Yet by other measures,

the band isn't popular at all. Only one of their original albums has ever made the Billboard top

10 rankings. None of their 883 songs has ever become a popular hit on the radio are you starting

to see the parallel. If the traditional band business model is to generate hype through

media and radio airplay, and then monetize that hype through album sales and tours,

fish doesn't fit that model at all. Their album sales are minuscule and their radio airplay is

non existent. That is exactly the same for Jimmy Buffett. Fish doesn't make money by selling music.

They make money by selling live music. And that it turns out is a much more durable business model.

This wasn't some brilliant pre calculated strategy by the band or its managers.

It's the business model that sprung forth from the kind of music the band makes.

The band developed the kernel of this musical style during their first five years when they

played almost exclusively in bars. Slowly and organically, they grew their audience the same

for Buffett. Another thing that's the same as Buffett is this sentence. During this period,

they maniacally focused on improving the quality of their music through intense practice and frequent

gigs. At first, these gigs were relatively unsuccessful over time, their audience grew.

They were profitable before anyone in the music industry knew who the hell they were.

We even got to that part of the story, but that's exactly what's going to happen to Buffett's career

too. And with profitability came the freedom to make music on their terms. Jimmy made music on

his terms. He lived life on his terms and he built businesses on his terms.

And so let's go back to his fierce work ethic. One of my favorite lines from the essay I mentioned

earlier by Paul Graham on how to do great work is being prolific is underrated. Jimmy Buffett

was definitely prolific in a little more than a year and a half. Jimmy Buffett had recorded.

I'm just going to count them one, two, three, three full albums and then a soundtrack for a movie.

He played every coffee house, beer joint and student assembly room from Boston to the Keys

to San Francisco and back. He continued to work Nashville, whether Nashville liked it or not.

He could make a living in Texas. He had a beat up truck, a nice little boat and a minor hit.

He'd grown his one man band into two. He had his wit and his charm and went right back to work.

And so in addition to being a workaholic at this point in his career, he's also a control freak.

Jimmy did everything. Buffett didn't think that the art department could present his music better

than he could. He didn't think that someone else should write the line notes on his album.

He had a case file full of evidence that record companies didn't get him and couldn't figure him

out. Listen to what he says. So he's reflecting on this time of his life. He's saying this in 2015.

He says at that point in his life in his career, there was nobody out there but you.

And so multiple decades later, he's defending himself. He says against charges of narcissism.

Yes, I'm a confirmed narcissist because there was nobody back there who gave a shit at the time.

You were on your own and you better be good. He was the most take control artists that have

ever been around. And so when I got to this section, I've said this before, but if I had to distill

every single thing down to one sentence, right? What have I learned so far in the seven years,

300 and something books, all these episodes about the kind of mentality that these founders had.

And I would say you need to combine the work ethic of Kobe Bryant with the self belief of Kanye West.

Jimmy Buffett had an intense work ethic, but just as important was his relentless self belief.

And I think this point is so important to internalize this self belief access fuel.

Everybody around him at this point saying, Jimmy, don't do what you're trying to do.

Jimmy, don't chase your dream. What's wrong with you? No, we won't sign you. No, we won't play you

on the radio. And Jimmy saying that belief was my fuel, which you call narcissism. I needed

because there was nobody back then who gave a shit at the time. You were on your own and you

had better be good. And so the reason I point this out is because this is happening to Jimmy

in the 60s and 70s. It happened way before that. It happened to Henry Ford in the 1919s.

And it will happen to people today. One of my favorite lines or one of my favorite songs about

this is actually by Kanye. This is why he popped in my mind. And on his first album, he has a song

called Last Call. It's 12 minutes long. And it tells the story of him trying to achieve the dream

that he had just successfully achieved with the completion of his first album. The parallels

between Kanye's own story and Jimmy is spooky. Listen to what he says. Some say he's arrogant.

He's talking about himself. Okay. Some say he's arrogant. Can y'all blame him? It was straight

embarrassing how y'all played him. Last year shopping my demo, I was trying to shine. Every

motherfucker told me that I couldn't rhyme. I'm going to pause there. Some say he's arrogant. They're

saying the exact same thing about Jimmy, right? It was embarrassing how you guys treated me.

Jimmy was embarrassed over and over again by record executives, by radio people,

by everybody in Nashville. Kanye was shopping his demo, meaning his demo tape. Jimmy was trying

to play his songs. They were both after the same thing. And everybody around them, they use

different language, obviously, but everybody around them saying, Nope, you're not good enough.

But here is the difference. And this is what Jimmy Buffett Kanye West and all these entrepreneurs

that you and I talk about have in common. They have this relentless self belief, belief comes

before ability. Now, I could let these dream killers kill my self esteem or use my arrogance

as the steam to power my dreams. I use it as my gas. So they say that I'm gassed,

but without it, I'd be last. So I ought to laugh. He continues. I don't listen to the suits behind

the desk no more. That's Kanye. What is Jimmy saying? I'm not listening to you. You don't get

to define what I work on. You don't get to define if I succeed or not. And you could tell Jimmy,

believe that through his actions, because everybody's telling him, No, and what do you do?

The guy refuses to stop. Oh, you won't sign me. Cool. I'll go play this free gig in a student

union at Purdue at 12 o'clock on a Monday. And the similarities between Kanye and Jimmy Buffett

continue. So I don't listen to the people to the suits behind the desk anymore. You can't say

shit to me anymore because I just rock 20,000 people. I was just on tour. What is happening

in Kanye's career? He didn't even have a record deal at this point. He's going on tour with Taleb

Quali and all these other rappers. And he's playing shows for 20,000 people at the same time.

Nobody wants to give him a record deal. And so Jimmy's agent and managers seeing the same thing is

like, I go to the Jimmy shows, all these people, they're growing, the receipts, the ticket receipts

are increasing. And yet I go to the same record executives and the same industry veterans in

Nashville. And they say, Nope, Nope, Nope. What are you going to believe? And you and I know they

answer that question. You always believe the customers. There is demand for what Jimmy Buffett

is making. And the executives are too slow. And by the time they realize it, it's too late.

And so slowly, but surely Jimmy is finding a new way to make it in the music business. Another

thing that I haven't talked about yet, but he was obsessed with cost efficiency. I reference this as

an infinite runway earlier, but he talked about this. He's talking about it now. We're still on

like, let's say the late 70s, early 80s at this point. And he talked about it when he was a much

older man, when he was like 50, 60 years old. And at that point, he had been traveling, they called

it a, they said Jimmy Buffett had been moving his traveling carnival show across America for more

than 30 years. And he takes pride in doing it economically and efficiently. He was doing that

day one, and he was still doing that same approach 30 years later, he watched his costs. And so they're

coming to understand that chart performance and radio play alone will not define his success.

And because of his costs remain manageable, and he didn't have to sell that many records to make

money, and his record label was not spending much money on promoting him, that he was actually

turning a profit. In other words, he was building a successful business. Music would just happen to

be the first product, the first of maybe hundreds. We talk it to, I've tried to collect all the

different things that he produced under the Margarita brand and all the licenses, Margarita

Ville brand and the licenses. Yeah, like I can't even, you can't even find them all in one place.

It's incredible. But music more specifically live music was the first product. And when you hear

this description of this live show, right, his first product, I think they said he made

over his career, I think the number I pulled from like 2021, he had made over $800 million

from his tour. This is the beginning of it says he pretty much stayed on the road jamming more

hours and miles into each day than the laws of time and space would seem to allow. He had proven

himself capable of writing and recording music, putting together a band and keeping that band

on the road and getting it on stage each night, no matter what, everybody working for him and

everybody around him calls him the benevolent dictator. That is the name that he gave himself,

and that's how he approached his business. He liked being in charge and he liked being detail

oriented. He is a benevolent dictator. That's what he calls himself. And you can tell right from

the jump that he's smart. He keeps the main thing, the main thing. This is so smart. The ground rules

as he explained to everybody around him was simple. I don't give a shit what happens 22 and a half

hours of the day. The only thing that matters is the 90 minutes that were on stage. If you had a

shitty day, or if you're just dragging ass, I don't want to hear about it. Don't complain. What

matters is the 90 minutes on stage, the main kept the main thing, the main thing. If we take care

of this 90 minutes every night that we're on stage, and we do that for a long time, we'll get

every single other thing that we want out of life. The 90 minutes on stage every night is what made

Jimmy Buffett tick. And so it's because he stumbled onto this business model. It's because he watched

his costs. It's because he was maniacal about practicing and making his life so better and

making a profit, even though it was a small profit, right? But that profit gave him an infinite runway

and what that achieved is another maximum from the history of entrepreneurship. Stay in the game

long enough to get lucky. He is about to do that. This is the creation of Margaritaville,

the song. What will become the cornerstone of his billion dollar empire in his notebook

was a song Buffett began writing in Austin after drinking away an afternoon in a Mexican

restaurant in a strip mall. He was with his friend and they had a few hours to kill before

a flight. And so they had some margaritas. I started it and then I get off the plane in Miami

and I drive on the overseas highway to Key West. And on the seven mile bridge, there was a traffic

accident and I sat there for an hour and a half and I finished the song. He decided to call that song

Margaritaville. And so he takes the song and performs it for his producer. This is why I go

back to that maximum that you should believe that your opinion is more important than the

opinion of anybody else around you. His producer tries to get him to change the title. Luckily,

Jimmy did not listen to him. So they released the song, right? And then he's on. He's in the

Caribbean. He's, you know, when he's not on tour, he's fishing, he's drinking, he's writing music,

he's practicing his guitar. And so unbeknownst to him and it was completely unpredictable to him,

the radio starts playing Margaritaville. That's kind of weird. And then it automatically starts

getting steam and it starts looking like a hit. And he's in the Bahama. And he's like, Oh,

shit, we have to capitalize on this. So he says change of plans, go get your back,

you go get your ass back on the bus. And so he leaves the Bahamas to go back to United States,

right? To start this tour. This is an excellent line. It was time to tour and he couldn't possibly

have imagined as he lifted off from the Bahamas, that this tour would never really end. And so I

mentioned at the beginning the fact that one of the things you have to admire about him is in

addition to, you know, making millions of people happy with his work, building this great business,

building wealth for his family is the fact that he was respected by his peers. There's always kind

of great stories in the book. Like this guy's flying over Jamaica. He was a pilot too. He owned

a bunch of planes. He's like a whole like private Air Force and he's flying the plane himself over

Jamaica and they mistake, he's got Bono from U2 and the plane and they get mistaken for it,

like a drug smuggler. And so the Jamaican government tries to shoot down the plane,

not knowing that Bono and Jimmy Buffett are the ones on the plane. But anyways,

something that happens after this hit is the fact that he becomes friends with a lot of people in

his industry. And so he develops a true friendship with one of the biggest bands in the world at

the time, which is the Eagles. And so they let Jimmy start opening up for him. And so now he goes

from playing like, you know, the student union and bars and the small joints to literally playing

stadiums. And that's just another form of distribution because it gets him into in front of

some of the biggest audiences in the world. And so because of his friendship with the Eagles,

he meets Irving Azoff. He decides, hey, I'm going to put my career in this guy's hands.

This guy may be the best manager or agent that you could possibly have at this point in history.

They called him, this is the description of how they, other people would describe Irving Azoff.

They said he is the American dream taken by the balls. And so I want to go back to this idea

that Jimmy Buffett, one of Jimmy Buffett's heroes is Mark Twain. In fact, in his autobiography,

he lists these 12 books. Like if I'm stranded on a desert island, I'm never going to come back.

These are the 12 books I would take. And in there is, of course, work by Mark Twain.

But there's also similarity in the sense that you can think about what's happening in Jimmy

Buffett's life right now in his career. This is an inflection point. There was an inflection point

in Mark Twain's world as well where he's in Hawaii. He'd already written like one viral hit

and there's this diplomat called Ambassador Burlingame. And he gave Mark Twain, he's much older

than Mark Twain. Mark Twain is a young man at this point. And he gave him some advice that

Mark Twain would use for the rest of his life. He had 44 years left to live and he would use

this advice that he got from Ambassador Burlingame. And this was the advice, which you need now is

refinement of association. Seek companionship among men of superior intellect and character.

Refine yourself and your work. Never affiliate with inferiors. Always climb. Jimmy is doing that.

Jimmy is climbing. He releases the next album after Margaritaville. There's another parallel

with Mark Twain. They say it specifically. So he releases this album. It's really about his

grandfather, right? Son of a son of a sailor. That's describing his grandfather, his dad and Jimmy.

This album sold big with limited radio play and no hit single. And Buffett was selling out shows

across the country. He's become the Mark Twain of Southern music. And so he's constantly refining

who's around him. It says Buffett had developed a disinclination to hang around with fucked up

people. Everyone wanted to show Jimmy what a wild partier they were because he was so famous for

being a partier. And he just hated that. Buffett liked to party, but he had his stuff together

and he wanted to be around other people who did too. And so remember when Buffett said,

yeah, I may be a narcissist. He also understood something about himself, which I don't actually

think is a negative. He realized, oh, I'm addicted to applause. He would go out and, you know, go to

the Caribbean, like take a vacation or whatever the case is. But then he immediately, there was

like a yin and yang to his life. He's like, I have to take a break from the road and then I have to

get back to the road because I miss it. And he says explicitly, listen, I have a thing for applause.

I am addicted to applause. Now, using the word addicted, I am addicted to applause. If your

main business is a live traveling show that you're going to do for three or four decades and you do

30 to 35 shows a year, year in and year out, not missing any show. That addiction is a good thing

for his business because that addiction is what keeps him on the road for decades. This may that

addiction may be the cornerstone of this Margaritaville empire. And what's fascinating is all

this is happening to him. Like, yeah, he's going to have Margaritaville as a hit. But I think he

goes 37 years, something like 37 or 35 years, something like that, between his next hit, which

is going to be the song written in 2003 by Alan Jackson called it's five o'clock somewhere. And

so what's happening at this stage in his career is like, oh, okay, my career is not going to be

driven by hits at the top of the charts. And I'm not going to be driven by mass appeal. So I have

to find another way in. And the way he found in wind up being much more lucrative than if he had

pursued what he thought he wanted initially. And so now he's in his 30s. And he says, listen,

he'd released seven albums in six years and had to produce one top 10 single. Now one of those

albums had gone past number 10 on the album chart. Radio hadn't been able to deny Margaritaville. But

after that, it was like radio found the hole in the fence that Buffett crawled through and patched

it up. Fine. You put up a fence, we'll crawl our way through, we'll jump over it, we'll dig

underneath it, we are going to find another way. And that other ways to entrepreneurship,

that other ways realizing, hey, these are not fans, this is a brand. I am fulfilling a need that I

didn't even know existed because I was just fulfilling that need for myself. It says the need

for a Caribbean poet spinning palm trees and stiff drinks into middle class fantasy was an

accidental discovery. And why did I say that's more lucrative because fashion changes, musical

tastes changes. But if you love the person that doesn't, I'm going to get there in a minute.

This is what I mentioned earlier that Buffett is an entrepreneur for sure. His product, his first

product just happened to be live music, but he's got all these people around him that had experience

in the music industry. And they keep warning him and other people around him like, listen,

man, people are want to be musicians or diamond dush and the people that last are the ones that

transition from artists to businessmen. They understand they think like a businessman. You

hear Buffett talk, he's clearly talks like an entrepreneur. And so he talks about, there's

just one guy that had like a, he was a talent agent. He just knew everybody in the business.

He was very famous in the 50, 60, 70s. And this is his warning. He says, there's a couple things

that I'm going to pass on to you from my experience. You're going to meet a lot of talented young people

and a lot of them are going to be one hit wonders. And you know why? They simply don't have the

intellect to deal with becoming a businessman. And so that continues to push Jamie Buffett down the

path that he's already started. He's like, my business is not hit driven. It's not radio. It is,

I'm in the live music business. And then he's going to accidentally discover a way to turn the love

of that show that he has into this business empire, which again, this is not a fat, get rich, quick

thing. You know, this is like, it says something, I think I mentioned this earlier, it's like,

he was an over and in terms of business, he was an overnight success 30 years in the making.

And so now we're in the 80s and they're talking about the overall trends. This is so fascinating

because mainstream tastes for music genres are going to change, right? They're going to change

by the decade, maybe by the year now, maybe by the half decade. Buffett was immune to this

because it's not about the music. It's not, it's about him. And so they talked about, you know,

they went from the age of singer songwriters, then they went, there was disco and then there was punk

and then there was this thing called outlaw country. And so all these people, these one hit

wonders are coming and going and Jimmy Buffett is sustaining. It says he'd built an audience and

that audience couldn't have been genre dependent because he didn't have a genre.

Why would a new decade of changing taste change that? And a way to think about that is Buffett

was the genre. Make no mistake about it. And it is said explicitly in this documentary watch,

he is a cult leader. You could mistake him for the leader of some strange tropical cult. It is a

cult of personality. It is built around him, not of any, not built around any genre of music,

not built around any changing fad. There's very few people, very few artists that understood

their fans or their customers as well as Jimmy Buffett does. You look at any great

business, they understand their customer very, very well. Jimmy just applied that to fans in

the audience. And so there's many examples where this, these fans in this market is pulling the

product out of him five years has passed, right? So in the last five years, since he released

Margaritaville, he made five more albums. Being prolific is underrated. Five years and as many

albums since Margaritaville, Jimmy Buffett was still the man from Margaritaville. He signed a deal

with Miller Beer and recorded a jingle. He records a commercial for Miller Beer. At the shows,

the commercial was so popular that they request him to perform the commercial like it's one of his

hits. How crazy is that? And then this is what he says. This is what I mean is like there are

very few artists who understood their fans as well as Jimmy Buffett did. Responding to a request

to sing the commercial, Buffett said, yeah, we'll do the commercial. Yeah, that was the closest thing

I've had to a fucking hit in five years. Here you go. You ask for it, you get it. If you listen

to your customer base, they will pull the next product out of you. He talked about this. He meets

this guy. They talk about this in documentary. He comes, he goes to the same cities over and over

again, which again, that is so important because if you went to the Atlanta show last year, you'll

go to Atlanta show next year. And then as he ages, you went to the Atlanta show for 10 years.

Now you're not, you know, now you're not in your twenties to thirties. Now you have a kid. Now your

kid is going with you. It is literally generational. That's how crazy it is. So he'll go through these

towns and he goes in the store one day and the guy that owns the store just happens to say,

oh, you're Jimmy Buffett, come here. Like I got to give you a big kiss. I love you. And the guy's

like, why? He goes, because every time you come to town, you see these Hawaiian shirts that I'm

selling, he goes, I can't keep them in stock. They buy every single one. And Jimmy's like,

oh, I guess I should make my own Hawaiian shirts. And he starts making like Buffett, he starts out

with the Jimmy Buffett merch. And he got that idea because he'd go to these towns and people would

make like bootleg Jimmy Buffett merch. And he's like, they're not even spelling my last name

correctly. Surely I could do a better job than that. And even though his name was misspelled,

they couldn't keep the t-shirts in stock. The market is pulling the product out of him.

So the early 80s from, let's say 1982, 1984, 1985, almost 15, remember, we're almost 15 years

into his career. Jimmy is now 38 to 40 years old. This is when he starts all wait, we can,

like, we're going to do shirts, we're going to do a book, he had an idea for a movie,

he's getting paid to promote alcohol, realize as well, why don't I just do a deal directly with

Anahear's a Bush? He licenses out the name to this bar called JB Margaritasville, or JB's Margarita

ville in Alabama. They wind up, what happens? Well, if you go there, what do you think they're

sell a lot of? Do they sell a lot of Margaritas? Yeah, of course they do. Do they sell a lot of

t-shirts? Yeah, of course they do. That business actually goes out of business because a bunch

of hurricanes hit the Gulf Coast. And so then he's like, oh, wait, this, this is fascinating. Like,

maybe we can run this playbook the next year. So he's talking, he's back in Key West, this is 1985.

And one of his friends who goes by the nickname of Sunshine Smith was getting foreclosed on our

house. And so Jimmy goes up to her, he says, Hey, why don't we just put up a t-shirt store,

put my name on the roof? And if it makes money, fine. And if it doesn't make money, fine.

This is the humble and simple launch of Margaritaville, the business, the actual brand, right?

He's going to wind up working on this for the rest of his life. He's got 38 years, 38 more years to

live at this point. And so they open a 500 square foot t-shirt store. And it evolved from there.

Then he goes back to this idea, hey, I need to have control my own distribution, right? I got

stiff by the mafia in the jukeboxes. So he starts this newsletter. This is what it's time

with newsletters, rational, physical things that you mail to people. But what happens? You're mailing

this to people, now you have their names and their addresses, you know, where they live.

That newsletter was first published in 1985. It's called the coconut telegraph.

And so everything he does feeds on everything else. The more he tours, the more t-shirts he

sells, the more licensing agreements he has, the more people that want him to promote his products,

then he's going to have his own products. And because he's sitting in these same cities year

after year after year, what is that allowing to happen? Compounding to take place. The math

suggested, remember, he is now probably 10 years since he's a hit. This doesn't make any sense.

How is this guy not having any hits in his business is more valuable every year. The math suggested

that Buffett's career should be waning. Instead, the crowds were younger. They were more enthusiastic

and they were bigger. This is the point it was making earlier. They're there for him,

not the music. Jimmy is Margaritaville. Margaritaville is Jimmy. The parrot heads,

which is the name of his fans, would stick with Buffett regardless of musical fashion.

Jimmy Buffett was Margaritaville. This is what the talent agent and the manager said.

Asof said only twice in his career had he been involved with what he called world building.

Margaritaville was world building. And so now almost two decades into his career, he's 40.

He's like, I'm not compromising anymore. He made one more run. He tried to make like a country,

like a traditional country album. So Nashville would play on the radio a few years ago. He's

like, I don't need to do this. No more compromise. I never really was a country act.

When they pitched the whole thing to me, I said, I'll give it one last shot. I'm thinking radio

means that much and it didn't work anyways. So I went back to doing what I wanted to do. You know,

I really didn't think I'd live to be 40. Now that I'm here, I've decided that they can't tell me to

do anything. Buffett wouldn't worry about genre. He would focus on audience and focus on that he

did for decades. This is crazy. 22 years. These are exciting times for me. I've been doing this

for 22 years. I'm just a saloon singer who's grown up. And I think audiences can relate to

this. This is about the idea that the audience aged with him. So they were asking him like,

what's a typical day? I write, play guitar, eat, read, sing and fish. I've noticed hangovers

are starting to feel like recovering from surgery. And so this is when he mentioned earlier that he

drank a lot less and he stopped doing drugs completely. And so he says he hit this one time

where he talks about really anybody that's dedicated to their crafts. There's something I

heard Kobe Bryant say that one time where he was asked by a modrishad. He's like, don't you ever,

aren't you ever worried about letting down the fans? And he hit a modrishad with like the stanky

face. And he's like, and what he said was fantastic. He goes, no, their expectations will never be

higher than my own. I love that idea that nobody should have higher expectations than you do for

yourself. We see an example of this here. He played back to back nights at Red Rocks in Colorado.

And they got so drunk the night before it says he still hadn't recovered by the time they hit

the stage. I made it through the show, he said, but I was mad at myself for not giving the crowd

its money's worth. Nobody in the crowd knew, but I sure did. And so again, that's another form of

discipline. You know, the fact that he might like to party, you might like to drink, obviously like

doing drugs. He's like, well, if this is getting in the way of the quality of my work, then that has

to be eliminated. So by the late 1980s is when they branch out into restaurants. This is crazy.

I had no idea they did the revenue that they do. For a few years, the restaurant in Los,

the Margaritaville in Las Vegas was the highest-grossing restaurant in the United States.

The Margaritaville outside of Universal Studios in Orlando is one of the highest-grossing,

I think it's the highest-grossing restaurant in Orlando, which is obviously, I think the,

has the most visitors, the most tourist visitors every year. But again, it just starts with one,

it always starts with one. Now they have tons of restaurants, they have hotels, they have resorts,

they're real estate developers, they have their own cruises, they have retirement home communities,

they have hundreds of licensees. And this is how he's making, you know, 30, 40, depending on the

year, personal income. Like his equity, the equity value in the companies is over a billion, made

him a billionaire. But the actual income, the cash flow he was getting was crazy, 30 million

some years, 50 million, $70 million a year. And so he partners up with this guy, Kevin Boucher,

who I think is still running Margaritaville now. They realized like, okay, who are we going for?

He says they aim for a middle-class crowd, not too exclusive, but not too cheap. They wouldn't

price anyone out, but they would not invite sloppy drunks. And so they open this first restaurant

in 1988, and the very first year that restaurant does over a million dollars in sales. And so he

picks his partners very carefully, he picks what he's going to do very carefully. And he says,

I remember supply and demand as the one and only Jimmy Buffett, he understood what his fans wanted

and controlled the supply. And based on his own experience, he knew that true success took time.

That's what's wrong with the world these days. Nobody wants to put in the time it takes to be

legendary. Mythology is not fast food. And so when Jimmy and his partner looked out at the crowds,

the millions and millions of people that come to his shows every year, they realized, oh,

this isn't just a crowd. These aren't just fans. This is a brand. These are people that already

believe in the Margaritaville ethos. They're interested in travel and leisure. And so they

start building this restaurant and hospitality empire. And then other people who are actually

fans of Buffett actually help him along the way. So Edgar Bronfram Jr. This is the son. I did a

podcast on his dad who founded the Bromperman family dynasty. They are the family owned sea

grooms and they branched out into a bunch of different media properties. But now this is

his son many years later, actually gets in touch with them. And he's like, Hey, can we license

Margaritaville and build a restaurant outside of the Universal Studios Park in Orlando? And that's

where they're like, Oh my God, there could be a very big business in these big box restaurants.

And so then the casino mogul in Vegas, Steve Wynne, Steve Wynne happened to be a big Jimmy

Buffett fan. And so he's like, if you open a Margaritaville in Las Vegas, I'll do that deal

tomorrow. And the size of some of these businesses may surprise you like the first year that restaurant

in Orlando did $18 million in sales. And so I found an interview that the CEO and Jimmy's long

term partner, this guy named John Colin gave a few years ago that describes this. So this is,

this is, I think this date is like two years old, but they had 33 hotels, resorts and other lodging

concepts, 150 restaurants, bars and cafes. They take an asset light but hands on approach. So what

does that mean? Margaritaville Holdings intuitively adopted an asset like model, where it licenses

its intellectual property to owners and operators via franchise agreements. Unlike most other

franchisors, Margaritaville is hands on about things like hiring the design firm that you have

to use, and even such details as which pillows go on the guest beds. And so on his own, slowly and

organically, he's growing this audience, he's growing this business. And again, we always talk

about staying the game long enough to get lucky, because you have no idea like you have future

opportunities, if you can stay in the game long enough to get lucky, there's going to be future

opportunities that are unlocked that you can't possibly predict. And one of them is the fact

that Alan Jackson, this huge country star in the early 2000s, really liked Jimmy Buffett. And so he

does this song called it's five o'clock somewhere. And he invites Jimmy Buffett to get on the song.

I think Jimmy's only on the song for like 30 seconds or 40 seconds. And this song goes crazy.

It spends eight weeks in the summer of 2003 at number one, it wins a Grammy, it wins a country

music association award, it wins an award of the Academy for country music award for single of the

year and video of the year. This line is hilarious says three decades after Jimmy Buffett arrived

in Nashville from Mobile, Alabama, he was an overnight country music sensation. Why is that

important? Because millions and millions and millions of people different new people, people

that may not have known who Jimmy Buffett was, hear the song. There's a Margaritaville ad at the

end of the song. It talks about Hey, it's always five o'clock in Margaritaville Buffett said,

I've been to Margaritaville a few times Jackson replied, they have a full on conversation at the

end of the song about Jimmy's business. You couldn't pay for advertising like that. And so now he

has this huge swell of new fans that didn't know him. And so what's the difference? What difference

does this make? He releases a new album. Remember, he started in the 1960s. This is 2004. He drops

this album called License to Chill. And it's his first number one album on Billboard's album chart.

Think about this. Buffett's first number one album took him 30 years to do. That explodes his

popularity. It also explodes his business. Now the deals are bigger. Like you're doing a restaurant

that may be doing 20 million a year in sales for one restaurant, you know, they have 150 of them,

whatever it is. But now they start building these massive resorts, they build a resort called the

Margaritaville Beach Resort. It's actually in South Florida. It costs 200 million to make 200

million. And that's just one property. This explodes his tour business as well. Between 2000 and 2009,

he was the 10th highest grossing act in the country. The other people on the list are people

like Bruce Springsteen, The Rolling Stones, U2 and Elton John. They start a line of cruises.

They start selling their licensed product on the home shopping network. They build a hotel and

casino in Oklahoma. They have their own line of margarita machines. They sell tequila. He starts

Lanshark beer. He sells bicycles, hammocks, bedding, luggage, candles, online games,

dozens of other products and more than 3 million cases of Lanshark beer a year. Over 15 million

people a year visit his restaurants, his hotels, his casinos and his resorts. Incredible. This is

where we'll end. He's been doing this all of his life from the earliest days of his career.

Four decades on, there's still nobody who understands who Jimmy Buffett is and what Jimmy

Buffett does better than Jimmy Buffett. It was the little details about dealing with vendors,

dealing with promoters, dealing with different concert halls, dealing with sound systems. And

when he got somebody who was good, he hung on to them. And if they started to screw up, which

happened when they were parting too much and they took it for granted, he knew he was very detail

oriented. He just paid attention to shit. By any reliable measure of pop stardom, Buffett shouldn't

have had the career he's had. Margaritaville was the 14th biggest hit of 1977. He should be going

out and playing at 3pm in the middle of a state fair. If I ever had to defend myself for my career,

Buffett said, I would only say that the most bitter artists I know are those who had the chance to

jump through the hoop and chose not to take it. They stayed on as a coffee house singer,

but I jumped through not knowing what was on the other side. And when I got there,

I had to deal with it. It wasn't happily ever after. I was just getting started.

What an incredible story. If you think about where he started and where he ended up,

that is where I'll leave it for the full story. Highly recommend buying the book. If you buy the

book using the link that's in the show notes in your podcast player or available at founderspodcast.com,

you'll be supporting the podcast at the same time. That is 323 books down 1000 ago,

and I'll talk to you again soon.

Machine-generated transcript that may contain inaccuracies.