The Biography of Jimmy Buffett

1. 0:00 – 3:53

   A Life in One Paragraph and the Biography's Scope

   1. DSDavid Senra0:00

      "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. Barts. 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 F-14 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 Fifty. That is not the book that I'm gonna talk to you about today, although I did read it to prepare for this podcast. 99% of the stuff I'm gonna 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, and 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 3:00 PM 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 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 wanna read one more passage from his autobiography, which I absolutely loved. And he was asked, "What are you gonna 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 1,000 ports of call behind me, and I hope 1,000 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."

2. 3:53 – 7:02

   Captain Buffett and the "Start Here" Chart

   1. DSDavid Senra3:53

      So I wanna start with his father. He has a... He's gonna have a rather tumultuous relationship with his dad. Uh, they actually are estranged for quite a while, and I think Jimmy wasn't in, uh, it 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, 'cause that's exactly what his grandfather did. Jimmy Buffett wasn't the first Buffett to set off for adventure. That would've been his grandfather, the former sea captain. His grandfather ran oil and ammunition to Europe during World War I. 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, the world by sea. Jimmy would do some of that later in life as well. And 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 fil- father has Alzheimer's, and they go back to Nova Scotia shortly before he dies. And they just wanna see, like, 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, the, the decisions that you and I make today w- can resonate through the generations. And so Jimmy's asking his dad, "What'd you think of this day? We went and saw where the captain, uh, had grown up, where all his family is from." And his dad said, "Well, I'm just glad that he jumped out that window, or we would've 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, 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 rebelled. He's like, "No, I don't. I want a life full of adventure." So he runs away and decides, "Hey, I wanna 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.

3. 7:02 – 10:48

   Rejecting a Conventional Life and Learning on Bourbon Street

   1. DSDavid Senra7:02

      So I wanna 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 k- sort of innate talent that is usually revealed early. So nobody knows who Jimmy Buffett is now. Doesn't have a record deal. Y- He's playing in, you know, bars and pizza joints and, uh, and on the street. But he's starting to, at this time, the center of the music universe, especially for the, the music that he thought he was gonna 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 'cause 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, uh, as a, as 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 gonna have a conventional, uh, existence. He actually talks about that multiple times. He's 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. Uh, 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 a young Jimmy Buffett reminded me of is actually, surprisingly, uh, Arnold Schwarzenegger has this great line in his biography, the one, the biography that, uh, 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. Th- 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 a, 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 is 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, the, 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 at 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, he believes at this time is the center of the music world. It's where he has to be if he's gonna succeed. He's going to accidentally realize that's not the case 'cause 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.

4. 10:48 – 13:36

   Billboard Magazine and Learning the Business

   1. DSDavid Senra10:48

      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 into 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 winds up meeting people, the music executives. He winds up meeting people working at the studios. He winds up work- 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, you have a hit song, but the guy that owned the publishing is making all the money. And Buffett is gonna 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, 20... There's-- The number's less than 20, and Buffett is one of them. And when I'm reading this part, this part reminded me, I did a episode on Jay-Z's autobiography, which is absolutely excellent. Uh, the book is absolutely, absolutely excellent. It's episode 238 if you haven't listened to it. But there is a time where Jay-Z's in his early 20s. This is reminding me of the, the, the lesson that Buffett, that Jimmy Buffett's 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 gonna learn this, and I'm gonna 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, you know, 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

5. 13:36 – 15:51

   Nashville Rejection and the Move to Key West

   1. DSDavid Senra13:36

      you'll see a bunch of sentences spread out through the book describing this time in his life, and it'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, 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 gotta get out of here." He said he hated Nashville. And he's like, "I, 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 gonna sign you. We're not gonna help you in any way." And so the maxim 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 in his music, and I'm gonna use the parallel that, that, that keeps popping in my, 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."

6. 15:51 – 19:22

   Wild Key West and Being the Only, Not the Best

   1. DSDavid Senra15:51

      The decision that Jimmy makes here is not obvious. It's-- it might be obvious in hindsight. The... I'm gonna describe what Key West was like in the '70s when he's there, okay? So it says, "Key West was and is for dreamers, schemers, and contradictions. It is hot, and the heat breeds its own sweet lunacy." So the kind of... He, he's, like, in a, a, a city or, like, a town of misfits, right? 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 o- something oceanfront in Key West, you know, 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, 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, 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 in at the 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 modern 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 in 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, 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 wanna 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 gonna move to if you wanna make it as a Southern or maybe country musician. But it's because of that 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've 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, you know, two decades into his career to then people realized, "Oh my God, he's got this massive following," is the fact that, what are you? You have no genre. You don't sound... You're not a folk singer. You're not doing rock and roll. You're not doing country. Decades before Peter Thiel said in Zero to One that if you wanna 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 this section, is like, "Oh, this guy's got infinite runway."

7. 19:22 – 24:15

   Infinite Runway, Reps, and the Radio Problem

   1. DSDavid Senra19:22

      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, 'cause 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, 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. There- I'm at the top of show business. There is nothing better than, than this." And so he's living in 100... Now he's in Key West, he's living in $150 a, 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 wanna play music and I wanna entertain people." He's now got infinite runway. And so his costs are low. He's got infinite runway, and now he can just, all he's dedicated to is practice, practice, practice. That's another main, uh, 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 him 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 out, 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 in the documentary, he was interviewed for the documentary I was watching. He said, "Yeah, I'm a, 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 artist 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 gonna be successful. This one guy that's trying to help him at this point is this guy named Don Light, and he's describing what's taking place and why Jimmy, even though he's c- 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 wanna sign him? Why don't they wanna put resources behind him? And so he says, "Record, uh, labels looked 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, sell. 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 I was never categorizable." That's what they would tell him. "It is ironic that I 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, it made me think of Bob Dylan's autobiography that I did all the way back on episode 259, 'cause Bob was talking about this, and he was talking about the people who were asking him, 'cause his sound was just so different and so odd. And so it says, "Hey," uh, 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 be- uh, 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."

8. 24:15 – 29:35

   No One's Eager to Fix a Cash Machine: Dylan, Dyson, and Self-Made Paths

   1. DSDavid Senra24:15

      Go back to episode 300, James Dyson. Still my favorite book, Against the Odds, an autobiography by James Dyson, is still my favorite book out of every single book that I have ever read for this podcast. What, what was James' mistake? Oh, great, James, you invented the world's first cyclonic vacuum. Who did you try to sell it to? You tried to sell it 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 fi- 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, there's, you're not categorizable. You- we're not putting any marketing dollars behind you. We're not putting you 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 be- 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 on 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 he'd 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 gotta 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 him 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, uh, in the first, like, ten 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 c- 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 liked those. They paid to hear him talk as much as sing." Again, they're not just buying music. They are there for him and anything that he does. He had no idea. It's gonna take, like, 15 years, maybe 10 or 15 years from where we're in the story. So he actually turns that into a business, and that's what allows him. The business supports the music. If he w- just did music, he would have never been able to survive. He just doesn't know that yet.

9. 29:35 – 33:51

   Jukebox Mafia and the Phish Parallel

   1. DSDavid Senra29:35

      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 gonna be rich. I'm gonna take this money from the song, and I'm gonna 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 p- 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, and it's 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 spread through 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 the 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 had 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 would r- 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 Phish, 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 Phish. And so Phish is mentioned in the book. There's actually a lot of similarities in between the way they built their business and the way Jimmy built his business. And so this article's several years old, but it says, "Over the past four years, the rock band Phish 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, Phish doesn't fit that model at all. Their album sales are minuscule, and their radio airplay is nonexistent." That is exactly the same for Jimmy Buffett. "Phish 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 haven't even got to that part of the story, but that's exactly what's gonna 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.

10. 33:51 – 39:05

    Work Ethic, Self-Belief, and Kanye's Parallel

    1. DSDavid Senra33:51

       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 gonna 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 l- reflecting on this time of his life. He's saying this in 2015. He says, "At that point in his life and 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 artist that I've 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 acts as fuel. Everybody around him at this point is 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's saying, "That belief was my fuel. What 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, it happened way before that. It happened to Henry Ford in the 1919s. 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 gonna 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, 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 desks 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 believed that through his actions, because everybody's telling him no, and what did he 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 he says, "Listen, I don't l- I don't listen to the people, to the suits behind the desk anymore," right? You can't say shit to me anymore because I just rocked 20,000 people. I was just on tour. What is happening in Kanye's career, right? He didn't even have a record deal at this point. He's going on tour with Talib Kweli 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 manager is seeing the same thing. He's like, "I go to the Jimmy shows. All these people, they're growing. The receipts, uh, the ticket receipts are, 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 gonna believe? And you and I know the answer to 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.

11. 39:05 – 42:08

    Cost Discipline, the Benevolent Dictator, and the 90 Minutes

    1. DSDavid Senra39:05

       Another thing that I haven't talked about yet, but he was acce- obsessed with cost efficiency. I referenced this as an infinite runway earlier, but he talked about this, he's talking about it now. Uh, we're still in 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, uh, 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 that his costs remained 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 was just happened to be the first product, the first of maybe hundreds. Wait till I get to... I, I've tried to collect all the different things that he produced, uh, under the Margarita brand and all the licenses, Margaritaville brand, and the licenses he had. 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. 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, uh, 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 we're on stage. If you had a shitty day or if you're just dragging ass, I don't wanna 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 live show better and making a profit, even though it was a small profit, right? But that profit gave him an infinite runway, and it, what that achieved is another maxim from the history of entrepreneurship. Stay in the game long enough to get lucky. He is about to do that.

12. 42:08 – 48:00

    Margaritaville, The Eagles, and Climbing

    1. DSDavid Senra42:08

       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 maxim, 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 release 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 pr- he's practicing his guitar. And so unbeknownst to him, and it was completely unpredictable to him, the radio starts playing "Margaritaville." He's like, "Oh, that's kind of weird." And then it automatically starts getting steam, and it starts looking like a hit. And he's in the Bahamas. He's like, "Oh, shit, we have to capitalize on this." So he says, "Change of plans. Go get your back... 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, 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, this great business, building wealth for his family, is the fact that he was respected by his peers. There's, like, all these kind of great stories in the book. Like, this guy's flying over Jamaica. He was a pilot, too. Uh, he owned a bunch of planes. He has, like, his own, like, private air force, and he's flying the plane himself over Jamaica, and, uh, they mistake-- He's got Bone- Bono from U2 in the, uh, the plane, and they get mistaken for, like, a drug smuggler. And so the Jamaican, uh, 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 this 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, and these 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 gonna 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 wanna 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 gonna come back, these are the 12 books I would take. And in there is, uh, of course, work by Mark Twain. But there's also similarity in the sense that you could think about what's happening in Jimmy Buffett's life right now and 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's 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. "What 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." Lit- there's another parallel with Mark Twain. They say it specifically. So he re- releases this album. This is 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 pa- and, you know, go to the Caribbean, like, take a vacation or whatever the case is, but then he'd immediately, he's like, uh, 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'm 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 gonna have margarita, but it, "Margaritaville" is a hit. But I think he goes, uh, 37 years, something like 37 or 35 years, something like that, between his next hit, which is gonna be, uh, 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, he's like, "Oh, okay, my career is not going to be driven by hits at the top of the charts, and I'm not gonna 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.

13. 48:00 – 56:00

    From Fans to Brand: The Cult of Personality

    1. DSDavid Senra48:00

       And so now he's in his 30s, and he says, listen, he'd released seven albums in six years and had produced one top 10 single. Not 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 way is through entrepreneurship. That other way is 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 taste changes. But if you love the person, that doesn't. I'm gonna get there in a minute. What, 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 that wanna be musicians are a dime a dozen. The people that last are the ones that transition from artist to businessman. They understand. They think like a businessman." You hear Buffett talk, he's clearly, he talks like an entrepreneur. And so he talks about, there's this one guy that had, like, a, he was a talent agent. He just knew everybody in the business. He was very famous in the, uh, '50s, '60s, '70s, and this is his warning. He says, "There's a couple things that I'm gonna pass on to you from my experience. You're gonna 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 Jimmy 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 gonna 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, the, it says something, I think I mentioned this earlier, it's like he was an over- in, 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, 'cause mainstream tastes for music genres are gonna change, right? They're gonna 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 j- it's about him. And so they talk about, you know, they went from the age of singer-songwriters. Then they went, there was, uh, 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 I 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 and this market is pulling the product out of him. Five years have passed, right? So in the last five years, uh, 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, the next product out of you. He talked about this, uh, he meets this guy, and they talk about this in the 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 the 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 20s or 30s now. 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 gotta give you a big kiss. I love you." And the guy's like, "Why?" He goes, "'Cause 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 then he starts making, uh, like Buffett, he starts out with, like, Jimmy Buffett merch, and he got that idea because he'd go to these towns and people would make, like, bootleg Jimmy Buffett mer- 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... Now remember, we're almost 15 years into his career. Jimmy is now 38 to 40 years old. This is when he starts, "Oh, wait, we can, like, we're gonna do shirts. We're gonna do a book." He had an idea for a movie. He's getting paid to promote alcohol, realizes, "Well, why don't I just do a deal directly with Anheuser-Busch?" He licenses out the name to this bar called JB Margaritaville, or JB's Margaritaville in Alabama. They wind up, what, what happens? Well, if you go there, what do you think they 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. Th- that, uh, business actually goes out of business f- 'cause 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 her 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, the business, the actual brand, right? He's gonna wind up working on this for the rest of his life. He's got 38 year, 38 more years to live, uh, 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 of my own distribution, right? I got stiffed by the mafia and the jukeboxes." So he starts this newsletter. This is when it's the time when newsletters were actual physical things that you mailed 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, f- 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 gonna have his own products. And because he's hitting 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 had a hit. This doesn't make any sense. How is this guy not having any hits and 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 I 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. Azoff 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,

14. 56:00 – 1:04:08

    Building the Margaritaville Empire and the Late Hit

    1. DSDavid Senra56:00

       "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 it on the radio a few years ago, and 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 think in 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 what he mentioned earlier, that he drank a lot less and he stopped doing drugs completely. And so he says, he, he hit this one time where he talks about really anybody that's, that's dedicated to their craft. There's something I heard Kobe Bryant say that one time where he was asked by Ahmad Rashad, he's like, "Don't you ever, aren't you ever worried about letting down the fans?" And he hit Ahmad Rashad with, like, the stanky face. He's like, "Ugh." 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. Uh, 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, he might like to drink, obviously liked 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 Las-- 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, uh, I think the, 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 a ton 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, uh, licensees and, uh, this is how he's making, you know, 30, 40, depending on the year, personal income. Now, uh, like, his eq- 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 Bushier, who I think is still running Margaritaville now. They realize, 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 gonna 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 realize, 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 Bronfman Jr., this is the son. I, I did a podcast on his dad, who founded the Bronfman family dynasty. They, they are the family that owns Seagram's, and they branched out into a bunch of different media properties. But now this is, uh, his son many years later, actually gets in touch with him, and he's like, "Hey, can we license Margaritaville and build a restaurant outside of the Universal Studios park in Orlando?" And that's when 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 Wynn, Steve Wynn 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 Colan, gave a few years ago that describes this. So this is, this is, uh, I think this data's, uh, 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-light model. where it licenses its intellectual property to owners and operators via franchise agreements. Unlike most other franchisers, 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 stay in the game long enough to get lucky, 'cause you have no idea, like you have future opportunities. If you can stay in the game long enough to get lucky, there's gonna 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 at the, the Academy for Country Music Award for Single of the Year and Video of the Year. This line is hilarious. It says, "Three decades after Jimmy Buffett arrived in Nashville from Mobile, Alabama, he was an overnight country music sensation." Why is that important? 'Cause millions and millions and millions of people, different, new people, people that d- 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 5:00 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? He, uh, what, what difference does this make? He releases a new album. Remember, he started in 19- 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, 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 r- 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 LandShark Beer. He sells bicycles, hammocks, bedding, luggage, candles, online games, dozens of other products, and more than three million cases of LandShark 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.

15. 1:04:08 – 1:05:31

    Details, Defiance of Pop Logic, and Closing Thoughts

    1. DSDavid Senra1:04:08

       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 partying 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 3:00 PM in the middle of a state fair. "If I ever had to defend myself or 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 on your podcast player or available at founderspodcast.com, you'll be supporting the podcast at the same time. That is 323 books down, 1,000 to go, and I'll talk to you again soon.

Episode duration: 1:05:32