I’ve had this little blurb on my resume for over a decade, and this is a screenshot from my LinkedIn:

Believe it or not, I'm pretty sure that blurb helped me land my first executive SaaS role.

Jimmy Buffett passed away peacefully with his family on Friday, September 1. He was 76.

Buffett was a poet, a traveler, a performer, and a businessman.

He was polarizing. You either understood him, or you didn’t. There wasn't much in between.

His fans are known as Parrotheads, and it's easy to see why:

Fins to the Left! Fins to the Right!

Buffett never got much airtime on the radio and never won a Grammy for his work. Yet, he had a massive cult following.

He toured constantly, playing for throngs of loyal fans at every sold-out show.

His business ventures extended well beyond music. In the 1980s, he began to leverage his fun-loving, carefree brand to build resorts, beer and liquor brands, and licensed merchandise.

Despite his limited acceptance by the mainstream, he died a billionaire.

Everything was designed around his ethos of having a little fun, as he explains:

…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.

Why am I writing about Jimmy Buffett in a B2B SaaS-focused newsletter? Because there are a few solid lessons to take from Buffett's life and work:

  • Be yourself. There's nothing wrong with mixing your personal passions into your professional life. We only live once. Bring your whole self to everything you do.
  • Don't try to please everyone. While mainstream media didn't give him much credit, Buffett was uniquely himself. His brand reflected who he was and appealed to a relatively narrow audience. But his fans were fiercely loyal.
  • Hard work still wins. Buffett portrayed a "play-hard" persona. But he was a CEO; His billion-dollar hospitality and entertainment empire employs over 5000 people today. In addition, he toured constantly. The song "Margaritaville" him on the map, but that was one of hundreds of songs he wrote. He released an album nearly every year in both the 1970s and 80s.

Greatness can be found in the nichiest of niches. But Buffett didn't find a niche.

He created one.

RIP, my fellow Parrothead.

See you on another road.

David Senra did a great podcast on the life of Jimmy Buffett shortly after he passed. It's worth a listen.

See you next week.

🦜 🎸 🤘