I’ve done a bit of smugglin’, and I’ve run my share of grass

I made enough money to buy Miami, but I pissed it away so fast

Never meant to last, never meant to last.

 “A Pirate Looks at Forty”.

     Despite the drug trafficking and financial irresponsibility referenced in his lyrics, the late Jimmy Buffett did not, in fact, piss it away.  He was a lot of things: pilot, sailor, musician, writer, businessman, and billionaire!  Unfortunately, he lost a battle with cancer and died in September 2023.  While most of us will never be famous musicians, there are a few business and financial lessons to learn from Mr. Buffett, and I mean the one on a boat in Key West sipping margaritas, not the one in Omaha sipping Coca Cola. 

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     I have no idea how I got into Jimmy Buffett’s music, but as far back as I can remember, I’ve been able to sing every word to the compilation album Songs You Know By Heart.  I don’t know any other albums, and I don’t consider myself a huge fan, but I really do know those songs by heart.  In 1999 I attended one of his concerts just outside of Chicago while I was in medical school and working at a Hyatt hotel.  I had so much fun tailgating with the die-hard fans called Parrotheads in the parking lot and then sitting on the grass listening to Jimmy bring the good vibes.  It was one of the best concert experiences I’ve ever had.    

     I read one of his books, Tales from Margaritaville, which I didn’t particularly like.  I’ve eaten at one of his restaurants a few times in Honolulu.  I’ve also always admired his business prowess.  Long before the musician-mogul was common, Jimmy was quietly building his empire.  Let’s explore a few business tips we can all learn from the late, great Jimmy Buffett.  

Learn to Be a Businessman

     From his early days in music, Jimmy was interested in business.  He claims he became the leader of his early bands not because he was the best singer or guitar player but because he paid attention.  “If you’re an artist, if you want to have control of your life…then you gotta be a businessman, like it or not.”

     With a minor tweak, Jimmy’s attitude applies to medical professionals.  If you are a physician, if you want to have control of your life . . . then you gotta be a businessman, like it or not.  Artists who do not take control of their careers will forever be at the mercy of the music industry.  The same can be said for medical professionals.  I wrote on this topic in the article, Medical Professionals, You Are a Business, Man


Develop a Loyal Customer Base 

     It’s easy to understand why artists such as the Beatles and Michael Jackson became so wealthy.  They were mega stars with countless hits and #1 albums.  But Jimmy Buffett?  His biggest hit was “Margaritaville,” which peaked at #8 on the Billboard Hot 100 in 1977.  So, how did he do it?

     Buffett developed a loyal fan base that supported him throughout the years.  His fans, known as Parrotheads, often traveled from city to city to watch him perform.  Buffett cultivated a consistent message of good vibes and good times on the beach, providing a respite from the stress of day-to-day life.  

     Your business should care deeply about its customers and develop a consistent message.  Buffet leveraged his loyal fan base as he expanded into other artistic and business endeavors.  He was able to turn his fans into paying customers.  This should be your goal as well.     

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Do Not Become the Brand

     The brand Jimmy created is centered around Margaritaville, a fictional beach town where you go to forget your problems and celebrate a carefree life.  Food, drink, sun, water, music, and relaxation are what you expect to find there.  Cleverly, Buffett did not brand himself.  You don’t have to be a fan of Buffett’s music to enjoy the idea of Margaritaville, which is why the company will live on now that he is gone.  

     For many medical professionals offering their services, they are the brand.  This limits the growth of their business.  You can only see so many patients, just like Jimmy could only perform so many concerts.  Find a way for your business to make money when you are not physically present.  A great place to start to think about this concept is the book Built to Sell, which I outline in My Top 10 Business Books Recommendations for New Business Owners.    

Diversify and Delegate

     Margaritaville Holdings was founded in 1985 in Key West, Florida, to sell Margaritaville-themed T-shirts and other merchandise.  Nearly 40 years later, the company licenses intellectual property rights via franchises to various businesses.  The brand now includes eponymously named restaurants, casinos, hotels, resorts, and even retirement communities!  Buffet was also involved in the creation and marketing of Landshark Beer for Anheuser Busch.  

     Buffett was also a decorated author, one of only eight in history to write a New York Times bestseller in fiction and nonfiction.  He owned his own record label, Mailboat Records, and was an accomplished sailor and pilot.  

     In business, it pays to diversify your offerings while staying true to your brand.  Margaritaville Holdings licensed a vast array of products, but all revolved around the Margaritaville brand, lifestyle, and aesthetic.  Buffett was involved but did not run the day-to-day operations of his holding company, leaving that to a dedicated executive team.  Additionally, by licensing his intellectual property, he partnered with experts in each field where his brand entered.  It’s hard to argue with the results.  He owned “only” 28% of the holding company at his death, which reportedly contributed $180 million to his fortune.  

Work Hard, But Not Too Hard 

     The title of the live album Buffett Live: Tuesdays, Thursdays, & Saturdays says it best.  By its release in 1999, Buffett would only perform on these select days.  Buffett was a hard worker and would tour up to the year of his death.  However, he followed professionally what he wrote in his lyrics: the idea that you’ve also got to relax and have fun.  “But I think it’s really a part of the human condition that you’ve got to have some fun.  You’ve got to get away from whatever you do to make a living or other parts of life that stress you out.  I try to make it at least 50/50 fun to work and so far it’s worked out.”

     Many of us are workaholics.  All work and no play can not only make us dull but can actually be counterproductive.  Listen to Jimmy’s advice and take time to relax and have fun.  You’ll return to work energized and more productive.  And if you don’t, as Jimmy sang, “Come Monday,” it’ll be alright.  

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     Whether you’re a fan of Jimmy Buffett’s music or not, I hope you now have a new respect for his business acumen.  He built a lifestyle brand around his most famous song long before the internet and social media made this common.  

     We can all learn some lessons from Jimmy.  Learn about business regardless of your profession, but especially if you are a high-income medical professional.  Earn a loyal customer base through your hard work while developing a brand, but don’t become the brand.  Once you find success, diversify into related businesses that stay on-brand.  And finally, work hard, but not too hard.  It worked for Jimmy Buffett.  His non-related billionaire friend once said, “I wish there were more Jimmy Buffetts, but there aren’t.  Tell Jimmy to keep me in his will!”  When it comes from Warren Buffett, that means you’ve been doing something right financially.  

     Thanks for indulging me by reading fun-to-write posts like this.  Subscribe to the blog so you never miss anything from Business is the Best Medicine.  As you know from posts like Our Vacation Home:  Dream Come True or Financial Nightmare?, I’m a big fan of the beach, so it should be no surprise that I like Jimmy Buffett.  I’ve wanted to write this post since he passed last year, so I’ll close with one of my favorite Buffett lyrics.  I always sing this anytime I have to leave a place I love.  I like to think Jimmy was humming it at the end.  

But I’ll be leavin’

In a little while

So close your eyes, and I’ll

I’ll be back real soon.