A Pirate Looks at Business

A Pirate Looks at Business

In my book, Make Your Move, I draw parallels from the example of how singer/songwriter Jimmy Buffett rose to stardom and then uber-business success by continually adapting his business into many businesses. We lost Jimmy Buffett this past week, reportedly from skin cancer that metastasized into lymphoma.

There is no doubt in my mind that his music will endure for a long time to come. As these newsletters are primarily about business, it can be instructive to reflect on how Buffett’s knack for adaptation can serve our own business plans.


Early on, Jimmy Buffett was a songwriter with a guitar. It carried him only so far commercially. When he added “The Coral Reefer Band,” his brand began to take off. Throughout his career, Jimmy Buffett was surrounded by talented musicians, including the ten-time Country Music Association Musician of the Year, Mac McAnally. When the band’s fame began to plateau in the early 1990s, Buffett branched into duets and collaborations with multiple high-profile country singers such as George Strait, Alan Jackson, Kenny Chesney, Willie Nelson, and many more.

Surrounding yourself with high-caliber talent can lift even mediocre talent.


Jimmy Buffett concerts were known to regularly play, “the big eight.” These were his eight most popular songs with fans such as Margaritaville, Fins, and Volcano. Surprisingly, only Margaritaville ever made it into the Billboard Top 10, peaking at number 8. The point here is that Buffett knew what pleased his audiences. Most of the biggest stars recognize this as well. Gary Vaynerchuck jokes similarly that “Bon Jovi had a pretty long run playing just nine songs.”

But, I’ll note, Bon Jovi didn’t run for over 50 years as did Buffett. How did that happen?

When the music was no longer producing the same commercial revenue year over year, Buffett recognized and took opportunities to branch into other lines of business while capitalizing on the Margaritaville brand. They include multiple restaurant chains, a cruise ship, retirement communities, resort hotels, a SiriusXM radio channel, and hotels, all maximizing the Margaritaville brand. Buffett was able to pivot to new things while remaining true to his roots and his audiences, even as those audiences began exposing children and grandchildren to his singular genre.

Whatever your product is today, your brand and reputation can offer alternative access to new markets and opportunities.


Jimmy Buffett’s career began when he left Nashville as a frustrated guitar player. He wanted more and believed in himself. His father was not exactly supportive of his early dreams. As Buffett’s career progressed, he repeatedly bumped up against resistance and ceilings that could have stalled his ultimate business prowess. Of note, he did not keep pushing on the same closed door, as so many people do. Buffett was successful in pivoting and shifting when required. From the outside, it looks easy. Persistence requires a blend of resolve, commitment, and smarts.

The point is not to never give up. Rather, acknowledge the market and move with it to continue to serve it. Meet the market where it is, don’t force your solution on it—but keep at it. At 76, Buffett was touring this year, had yet another new album whose release was imminent, and was building a new custom yacht—he had not sailed off into retirement.


As the eulogies flow for Jimmy Buffett, the words even the biggest global celebrities use include humble, generous, fun, friendly, caring, and giving. Too few know of Jimmy Buffett’s Last Mango Boatworks charities. He wasn’t just a friendly person, his charities encouraged everyone with his tagline, “See the good side.” 

Some of Jimmy Buffett’s song verses would occasionally be modified on the road to poke fun at a political issue, but he never publicly engaged in the drama surrounding politicians. One issue he directly engaged in was the preservation of the Florida manatee, a gentle giant of a sea creature that was on the verge of extinction in the early 1980s. Along with then Governor Bob Graham, public awareness was raised to protect this species.

Proceeds from Make Your Move support Freedom Fighter Outdoors (FFO), a charity formed and supported directly through the Last Mango Boatworks charities. FFO supports wounded veterans with unique outdoor adventures such as saltwater fishing and hunting. I’m proud to have even a small association with the efforts of such a unique entertainer and leader of our time, Jimmy Buffett.

If you’ve read Make Your Move, you know I first came upon Jimmy Buffett as a teen in South Florida where I learned to race offshore sailboats. His inspiration and depiction of a casual and comfortable lifestyle endured as I would chart my own career, business, and course of life. I hope you’ll take a moment to reflect on how the four points above might be affecting the success of your own business.

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