Life & Business Lessons from Jimmy Buffett

This summer I attended my 20th Jimmy Buffett concert.  The venue this time: Wrigley Field.
I’ve been a Parrothead- an avid fan - since 1991.  Here are 5 things you can learn from the Son of A Son of A Sailor.

There’s a saying in my business, “a niche can make you rich.”  Until 2003 when he teamed up with Alan Jackson for “It’s 5 O’Clock Somewhere,” Jimmy Buffett had only two career top 40 songs.  The most recent in 1977.  

Critics love to criticize the man’s music.  It isn’t artistic.  The chords aren’t advanced.  His lyrics are simplistic, sing along songs.  But sing along his legion of fans do.  Buffett is mega successful because he plays to the crowd to which he appeals. 

Jimmy Buffett says, “I sell escapism.”  His sales conduit:  song, products, restaurants, and even books.  Books?  Yep, he’s one of only eight authors to hit both New York Times best seller lists, fiction and non fiction.  That puts him in company with John Steinbeck and Key West’s other famous adopted son, Ernest Hemingway.  

The guy understands his value proposition.  He sells his fans a piece of real estate inside their own head.  Margaritaville is a place we all wanna go.  Buffett steers the ship.  

Jimmy Buffett delivers on his commitment to those who pay him.  I saw him in Indianapolis two weeks after the tragic events of 9-11.  Part way through his first set, Buffett paused to address the elephant in the room: “There’s lots of stuff I could say about recent events but the best thing I can do for everyone is play Jimmy Buffett music.”  

At Wrigley, he came on stage following a rousing rendition of “Go Cubs Go” wearing a Cubs jersey.  The 71 year old ran backstage and navigated the bowels of an old ball field to pop out in the world famous Wrigley Bleachers for his encore.  At this point in his career, Buffett could phone it in.  He doesn’t.  

I learned long ago, and clearly so did Mr. Buffett, there are four letters in the word “show” and eight letters in the word “business.”  Point: apply twice the effort to the business that you do to the show and you’ll be successful.  

The Buffett empire is expanding into real estate.   Margaritaville themed residential developments for active adults are springing up in multiple warm weather locations. 

Jimmy talks about honing his business skills in the early days while wheeling around Texas in a station wagon, booking his own gigs and brokering his own deals.  It worked.  Buffett the businessman is expected to earn $50 million this year.  His net worth is estimated around $550 million.  

Buffett talked once about his motivation.  As an ascending musician he was booked to perform at a Holiday Inn.  His warm up act was a well known performer whose career was in decline.  Jimmy said he never wanted to go through that.  Showbiz is fickle.   

Now he’s worth over half a billion dollars.  Presumably he could settle into one of his retirement communities quite comfortably.  But watch the guy in action and you truly get the idea he’s enjoying the life and business he created.  Something we should all strive for.  

Damian Mason is a businessman, speaker, farm owner, and Parrothead.  Find him at his One Particular Harbor or