A Legacy in Flip Flops

A Legacy in Flip Flops

by Adam O’Neill MBA, SPHR – Sr. Human Resources Consultant

September 2023

The music world recently lost a legend and it hit me particularly hard.  Having once performed on stage with Jimmy Buffett and the Coral Reefer Band, I consider myself to be one of his biggest fans – a true “Parrot Head” – Hawaiian shirt, flip-flops, and all.  In the days that followed his passing, his most zealous followers, including many well-known celebrities, paid heart-felt tributes to the icon.  Among the social media postings that poured in, what stood out to me was the fact that this man, in additional to being a wonderful songwriter and performer, was an even more brilliant businessman, building an empire worth Billions. 

Buffett penned popular songs such as “Margaritaville,” “Come Monday,” and “A Pirate Looks at Forty,” but many may not know that he was also a best-selling author, playwright, and founder of Margaritaville Holdings, LLC which owns several resorts, restaurants, casinos, cruises, planned residential communities, and merchandise outlets.  So, without delving into the many details of his music life, let’s look at some key takeaways that defined his career and business success:

  1. THINK POSITIVELY.  A people-oriented person, Buffett believed in himself and always gave his fans what they wanted (and were happy to pay for).  His songs struck a chord with his audience; lyrics that provided an escape from the troubles of the day and brought much needed joy into the life of the listener.  Among his many famous sayings is, “It takes no more time to see the good side of life than to see the bad.”
  2. KNOW YOUR CRAFT.  Buffett admitted throughout his career that his guitar playing was “adequate” and his singing ability was “fine,” yet neither was great.  But that didn’t matter, as what he may have lacked in singing and playing ability, he more than made up for in charisma and a drive to succeed.  Besides, his fans did not expect perfection – only a connection.
  3. FIND A NICHE.  Buffett pursued his passion regardless of popular opinion.  Born in Pascagoula, MS, he grew up believing that country music was his calling.  But when his pursuit of the “Nashville sound” in the 1970s didn’t quite feel right, he up and fled to Key West, redefining his brand and finding his own niche sound.  With his Gulf Coast, Caribbean style folk rock genre, he never generated a top 10 hit until 2003 when he collaborated with Alan Jackson on “It’s 5 O’clock Somewhere.”  But while Buffett’s unique songwriting remains somewhat unrecognized by music experts, one very well-qualified critic by the name of Bob Dylan includes Buffett among his favorite songwriters of all time.  Not a bad endorsement.
  4. EDUCATE YOURSELF.  If you’re familiar with his songs, you know he was no math whiz, but one business class at junior college taught him everything he needed to know about supply and demand economics to launch his music and merchandise business. PhD not required.
  5. ASSOCIATE WITH TRUSTWORTHY, COMPETENT PEOPLE. Buffett was business savvy and people smart.  He surrounded himself with individuals who were trustworthy and professional, and encouraged them to showcase their talents.  Great leaders know that the success of the team requires success of its individual members.

We can learn much from the life and career of Jimmy Buffett, and any budding entrepreneur would do well to read more about his business acumen.  I am convinced that the Margaritaville brand will continue to thrive well past his death, as his songs will continue forever.  Thank you, Jimmy, for the gift of your legacy.  Fins Up!


Acadia HR has been helping businesses locally and nationally since 1989 by delivering tools and resources to build efficiencies in their clients through personal, customized service. For more information on outsourcing options, please call 845.876.1987 or email sales@AcadiaHR.com.                             

Leave a Comment

Your email address will not be published. Required fields are marked *