What Would Jimmy Buffett Do?

Over the weekend, we were sad to learn that famed singer, Jimmy Buffett, had passed away at 76. Buffett was known for his island-inspired music, which provided dedicated fans and casual listeners alike a much needed respite from humdrum life in hit songs like “Cheeseburger in Paradise,” “Margaritaville,” and his collaboration with Alan Jackson in “It’s Five O’Clock Somewhere.” Buffett’s laid-back ethos struck a chord with fans. Eight of Buffett’s 30 released albums are certified gold, and nine are certified platinum or multi-platinum; he sold over 20 million albums in total. Despite his fame, Buffett never lost touch – the myriad of obituaries and commemorative messages reflect his deep familial values, intense curiosity, and genuine love for meeting new people.

And these posts had another, perhaps lesser-known, common thread: he was a tremendous businessman and a master world-builder, which is a topic we think about a lot at Slow. He cultivated an intense fanbase and constructed an entire universe (beyond music) for them to consume – and he made a ton of money doing it. He connected to his listeners so deeply they proclaimed themselves “Parrotheads” (arguably the boomer equivalent of Swifties?). Loyal and like-minded community is a prerequisite for world building, as the artist-fan relationship develops contours rich enough to transcend the music (or content) itself. He then parlayed his fame into various business ventures: the Margaritaville and Cheeseburger in Paradise restaurant chains, hotels, casinos, stores, books, cruise ships, liquor, and even retirement communities. In total, Buffett had amassed a net worth of $1Bn, making him one of the wealthiest musicians in the world.

A devoted Parrothead himself, Dave Portnoy of Barstool Sports captured it best (note: the whole blog is worth a read):

Now I know for those Jimmy novices you may be asking what does his beach bum lifestyle have to do with business or Barstool? Well despite his laid back persona he’s also one of the best businessmen of our generation. In fact when I first sold Barstool to Chernin Group they asked me who my business inspiration was. I had never been asked that question before but I answered without hesitation that it was Jimmy Buffett. He was nothing short of a genius in the way he was able to take his brand of storytelling and escapism and build an entire lifestyle brand out of it. Books, bars, casinos, restaurants, alcohol, merch etc. You name it he did. He built a fanbase and a culture and stayed true to it and monetized it. Exactly what we did with Barstool Sports and I always saw the parallels.

Portnoy is not alone in his admiration. Kygo and his team were also heavily inspired by Buffett, modeling Palm Tree Crew Holdings as the Margaritaville of dance music (and Buffett happened to be their first investor). Both Portnoy and Kygo recognized the massive business opportunity that emerges from a passionate community.

To many of his fans, Buffett’s ventures felt more like an extension (or even elevation) of his brand rather than a quick buck. On tour, for example, he owned the entire experience he provided; as a result, not only was he able to tailor his listeners' immediate universe, but also profit from the merch, food, and drinks (in addition to tickets). World building is most successful when grounded in identity – it wasn’t that Margaritaville retirement communities were prestigious but rather that they reflected the familiar, vacation-minded ethos found in Buffett’s music.

While a herculean effort to actualize, the respective ecosystems that Buffett, Portnoy, and Kygo have built offer a level of operating leverage that allows them to control their own destiny. And, as a result, their success isn’t only reliant on their laborious input or industry gatekeepers. Buffett will not only be remembered as an iconic artist and family man, but also as a consummate business mind and exemplar of brand power. For creators building their careers, Buffett represents the full spectrum of possibility enabled by authenticity and audience engagement.