Life gave Jimmy Buffett lemons… and he turned them into his very own Margaritaville!
A failed country artist, an Auburn University dropout, and a flop debut album. Sounds like a recipe for despair, right? Not for Jimmy Buffett!
This is a special Failure Profile episode on the fascinating journey of Jimmy Buffett, the iconic singer, songwriter, and businessman known for hits like “Margaritaville” and “Come Monday.”
Despite facing a rocky start— including college failures and a divorce— Jimmy’s resilience and innovation propelled him from dive bars to boardrooms, ultimately creating a $500 million empire!
Join me as I explore the turning points in Jimmy’s life: from his move to Key West, Florida, where he fine-tuned his “island escapism” lifestyle, to the breakthrough moment in his music career. Discover how he masterfully diversified his income streams and became an author, actor, and entrepreneur, all while staying true to himself.
But this episode is more than just Jimmy Buffett’s story; I’ll also reveal 5 tangible takeaways you can learn from Jimmy’s life so you too can embark on the path to your own paradise.
If you don’t have time to listen to the entire episode or if you hear something that you like but don’t have time to write it down, be sure to grab your free copy of the Action Plan from this episode— as well as get access to action plans from EVERY episode— at JimHarshawJr.com/Action.
[00:00] How did a failed country artist end up with a net worth of over a half a billion dollars legions of fans in an empire based on flip flops and margaritas? Well, stick around to discover the fascinating journey of Jimmy Buffett and how he turned setbacks into a lifelong vacation. Welcome to another episode of success.
[00:22] Through failure, the show for successful people. And for those who want to become successful, the only show that reveals the true nature of success. This is your host, Jim Harshaw, Jr. and today we're talking about Jimmy. Buffett. Yes, Jimmy Buffett, the late Jimmy Buffett. If you don't know, he died September 1st, 2023, age of 76, and he died of skin cancer.
[00:44] Sadly, if you don't know who he is, he was a singer and a songwriter, a businessman. He's a pop culture icon, especially known for his biggest hit. Probably it was Margaritaville. Another one was the song called Come Monday. Those were his two biggest hits, but this guy. Created so much amazing success. And there's so many lessons to learn from his story that I want to share today.
[01:09] And I knew a lot of these, I knew about them. I, one of the first CDs I bought when I was in college, I remember buying a Jimmy Buffett CD, Jimmy Buffett's greatest hits. And he's like one of those guys that everybody loves Jimmy Buffett music. Reminds me of Bob Marley. I mean, everybody loves Bob Marley.
[01:26] Everybody, nobody hates Bob Marley music. Well, it's, I feel like it's the same way with Jimmy Buffett music. And this guy created success in so many unique and different ways than any other musician out there. This is an example. His life is an example of how you can find opportunity, not just despite failure, sometimes because of failure, but you can take what you have now.
[01:51] And spawn all kinds of other opportunities for money and revenue and success on that side, as well as success in your personal life, like living a balanced life, like finding time to do the things that you love. So. He was a great example of that. So the more I did research on him about this episode, cause I was thinking about this episode after he died.
[02:16] And I'm like, I don't know if there's really anything to go on there, but the more I dug, the more I learned there's so much to go off of here. So I'm going to give you some really concrete, tangible takeaways, things that you can do in your life to figure out what the next step is for you in your career, to figure out.
[02:31] How you may want to pivot in, in the life or the lifestyle that you live right now. Are you going to get a lot from this? All right. So here we go. The life and lifestyle of Jimmy. Quick interruption. If you like what you're hearing here and you want to learn how you can implement this. Into your life, just go to JimHarshawJr.com/apply to see how you can get a free one on one coaching session with me. That's JimHarshawJr.com/apply. Now back to the show. So he was born in 1946 in Mississippi. He grew up mostly in Mobile, Alabama, and he had a lot of failures early on in his life. His first failure, that's documented, that I could find anyway, was when he failed out of Auburn.
[03:17] He went to Auburn University and failed out after a year, failed out of college. Eventually went back to college and got his degree a few years later, but he was initially a failure in college. And, you know, he graduated college. He wanted to be a journalist, but eventually made a shift to music shortly after college, but another failure was his first marriage.
[03:37] He got married in 1969 and he got divorced three short years later. So failure number two, his third failure early on in his life was his first album called down to earth 1970. It was a total commercial failure. So he has a marriage that ends in divorce, drops out of college after one year and his first album is a failure.
[04:00] Not exactly what you would think about of somebody who's going to go on to become a cultural icon with a half a billion dollar net worth. I mean, he did not start. I mean, he was. Playing to small crowds is living hand to mouth. There are times that he was playing in dive bars at small events, far removed from the success that he eventually went on to have.
[04:22] So think about you and your life and the, and the failures and the things that you've tried, or maybe you have some failures on your record. And you're thinking, yeah, boy, that that's, these things are lingering and holding me back and creating doubt. So did Jimmy Buffett. All right. So this was his early life.
[04:37] And then he eventually moved to Key West, Florida. And this was really a pivotal point in his life and in his career. He really fine tuned his image to reflect this beach. Combing sort of Island escapism lifestyle, which really became the hallmark of his brand and his sixth album. It took him until his sixth album till he really broke through.
[04:58] He had his breakout hit Margaritaville. The album was changes in latitudes, changes in attitudes as 1977. And this just became a huge hit. We came up like an anthem for beach lovers, right. And beach goers everywhere. And this was a turning point for him. And he sort of found his mainstream success there.
[05:19] And this is really where he built his empire around this concept of Margaritaville, this brand. Became restaurants, merchandise, he's had casinos with the Jimmy Buffett theme, retirement homes, a record label, cannabis, a video game, beer. I mean, it wasn't all around just that song and that word of Margaritaville, but it was his brand, the Jimmy Buffett brand.
[05:47] There was Landshark. Beer, which was a partnership with Anheuser Busch. Um, he partnered with a casino. He partnered with retirement homes. He created a record label. Uh, he invested in sports teams. He launched a Broadway musical, actually two of them. I mean, this guy found opportunity, right? And you can say, yeah, but he had money and he had fame and all this.
[06:08] Well. I mean, he had some, he created even more than there actually was there. I mean, there are plenty of artists out there who have reached some level of fame, right? At least what you think about his initial level of fame. I mean, he, he was mainstream, like that song became mainstream, but, but he wasn't one of the biggest bands out there.
[06:29] He never actually never really won any huge musical awards over his. 30 plus, you know, 30 some year recording career, he never won any huge awards. Actually, I think the first big one he won was it's five o'clock somewhere. He recorded that with, I think it was Alan Jackson. That was like in the early 2000s when he finally won like a significant, like it was a country music award, but he never really won these big awards.
[06:53] So he created success. He looked around him. And he found opportunities and you can do the same, like look around you. What opportunities, what unfair advantages do you have? We all have them. And Jimmy Buffett took advantage of his unfair advantages. And a lot of artists don't do that, right? They sing, they perform and that's all they do.
[07:16] Or you're an accountant and that's what you do. Or, you know, you're. A doctor, whatever it is, and that's all that you do. He took advantage and created multiple streams of revenue. He actually wrote two bestselling books. Also tales from Margaritaville, another one called, where is Joe Merchant? I don't know what that one's about, but he wrote two books and they were both bestsellers on the New York times bestselling list.
[07:37] So this guy branched out, he found opportunity. He created opportunities. He took, uh, took advantage of his unfair advantages. And we, like I said, we all have those. Now you say, Oh, well, man, things are really easy for him. Once he had that breakout hit. No, he had a musical that failed. His first musical was, uh, don't stop the carnival.
[07:57] It debuted in Miami, Florida in the 90, in 1997, negative reviews from the critics ran for six weeks, total failure. Well, that launched him into an opportunity down the road where there was another musical and it was called escape to Margaritaville. And that one had huge success, ran on Broadway, went on national tour.
[08:19] So he failed and he didn't say, ah, well, I guess musicals aren't. Something I'm good at. I shouldn't do that again. No, he actually failed at it and then created success because of that later on. I wish whenever I failed in my software business, I had a software company years ago called riot sports marketing.
[08:37] And I failed, man, I made so. Many freaking mistakes in that business. It was unbelievable. I was just stumbling my way through. I had no business, no knowledge of creating a software, but I did it anyway. And I failed so many times, but man, by the end of it, I had so much wisdom, so much knowledge. I was so prepared to develop another software.
[08:59] I had this belief that because I failed, I shouldn't do that again. I'm not good at that. And now looking back, I realized, gosh, I was actually far more prepared. And actually I'm thinking about creating an app and have other sort of designs and opportunities that I'm thinking about for my own business.
[09:18] Well, I'm actually more prepared to do that because of that failure. I learned so much through that failure. Jimmy Buffett learned in his, through his failure in his first musical in the second one became a hit. Now things still weren't always easy for Jimmy Buffett in 1994. He crashed his seaplane taking off.
[09:36] He was the pilot. He crashed his seaplane taking off near Nantucket. You know, it nosedived it flipped and luckily he swam away to safety. Here's another story that I come across when I was doing my research for this. And a lot of this is in Wikipedia and in just easy Google searches helps. And we'll, we'll list those as references in the action plan again, JimHarshawJr.com/action for that. But check this out, 1996. He's landing his seaplane in Jamaica and he's hanging out with Bono. It's, it's Jimmy Buffett and his family, Bono of U2 and his family. They land in Jamaica just off the beach and they're getting shot at by the Jamaican police, the Jamaican police are firing away at them.
[10:18] They mistook them. They thought there were drug traffickers and they thought it was a drug trafficking plane. And Bono and his family were totally rattled. They took the first plane out. They're like, we're out of here. Jimmy Buffett stayed, made amends with the police and they apologized and everything.
[10:33] And, you know, he just really downplayed the whole thing and he accepted their apology and just. It was okay with him, right? He obviously was a, it was a harrowing, terrifying experience, but he, he let it roll off his back and then he wrote a song about it. It's called Jamaica Mistake. Jamaica Mistake is the song that he wrote about that experience.
[10:54] If you look up the lyrics, actually, we'll, we'll have a link in the action plan where you can click over and find the lyrics. It's pretty funny that he made a song out of this. Terrible life threatening experience, but things weren't easy for him. It's easy for us from the outside, looking in, looking at these extremely successful people and saying, gosh, things were just easier.
[11:16] The road was just paved for a Jimmy Buffett or. Whoever it is that you're thinking about to create the success that they've created. Now, when I say success, I'm not just talking about financial success. I'm talking about life and lifestyle and legacy. By the way, I recorded an episode just a few episodes ago about legacy.
[11:35] Go ahead and check out episode number. 420 to hear my whole episode on legacy, how to create your legacy. And this is what Jimmy Buffett did, right? He built his legacy and you can build your legacy too. And, you know, despite your failures because of your failures, but what I want to give you now is our specific tangible takeaways that you can learn from Jimmy Buffett's life.
[11:59] And apply to your own life. Okay. There are five of them. First one is this success through failure. Yes. I know that's the name of the podcast. Jimmy Buffett's empire did not happen overnight. It was built on a series of failures on a series of experiments and, and risks calculated risks. It took grit. It took perseverance to create what he created this empire.
[12:23] He took risks. He had to fail in order to create this. And it's the same for you. Like Failure is going to be part of your experience. And you can say, well, I can't create success because of my failure, or you can say, I can create success because of my failure, you can create success because of your failure, and that's what Jimmy Buffett did.
[12:42] Okay. So that's 10 tangible takeaway. Number one is success through failure. Here's number two, follow your passion. I mean, this guy did not follow the blueprint for creating wealth and for creating success and for creating a lifestyle that he loved. I mean, his love for the beach and island life, it didn't just influence his music.
[13:02] It became his, his personality and his brand and his lifestyle, restaurants to retirement homes. I mean, and everything in between, this was his brand. He followed his passion. He created opportunity. I mean, how many, like I said, how many other musicians have done the same, created an empire and he's. Barnaby, not even close to a huge musician in terms of, you know, the high pride name, a hundred other musicians who are much bigger, who did not create this kind of, of brand.
[13:32] He followed his passion and made his own path. That's number two. Number three is. Diversify beyond music. This guy's an author. He's a businessman. He's an actor. He had multiple streams of income, multiple skills that he developed. He didn't just know how to play guitar and sing. He developed business skills.
[13:52] He developed networking skills and he was able to find opportunity everywhere because of that. Diversification. That was number three. Number four is this work life balance. His songs and his lifestyle kind of advocate for, for this, this taking it easy and enjoying life, simple pleasures. And, and certainly this guy worked really hard, but he also played hard.
[14:14] He had a good time. Right? This is something that should resonate with you. And, and, you know, it certainly does with me about family and, and life values and living life on your terms and not just living to work, but working to live, right? So that's number four, work life balance. And the last one is this authenticity.
[14:33] He was himself, his brand and his music. They've remained consistent over his career. He never tried to be somebody he wasn't. He failed it trying to become like a country music singer in Nashville. And he created his own really Island. I said, Island escape ism kind of beach music. He created his own almost your genre of music, right?
[14:58] He was authentic to that. So be. You be yourself. So what's your one takeaway? What is your one takeaway from this? What, what can you do? Like what's actionable for you in your life right now? I talked about the takeaways, success through failure, follow your passion, diversify, work life balance, be authentic.
[15:19] What can you take from this? I don't want you to just listen to this and say, yeah, that was a great story. I want you to actually take action on this. What's something you can do in the next 24 to 48 hours to put this into action in your life. I hope you enjoyed the episode. Go listen to yourself. Some Jimmy Buffett, figure out what your takeaway is.
[15:36] Good luck. Thanks for listening. If you want to apply these principles into your life, let's talk. You can see the limited spaces that are open on my calendar at. JimHarshawJr.com/apply, where you can sign up for a free one time coaching call directly with me and don't forget to grab your action plan.
[15:55] Just go to JimHarshawJr.com/action. And lastly, iTunes tends to suggest podcasts with more ratings and reviews more often. You would totally make my day. If you give me a rating and review, those go a long way in helping me grow the podcast audience. Just open up your podcast app if you have an iPhone, do a search for success through failure, select it, and then scroll the whole way to the bottom where you can leave the podcast a rating and a review.
[16:23] Now, I hope this isn't just another podcast episode for you. I hope you take action on what you learned here today. Good luck and thanks for listening.
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