Before he was a pilot, before he was a best-selling author, before he was a brand, Jimmy Buffett was an accomplished musician turned small bidness owner of a 450 square foot T Shirt shop in Land’s End Village at the foot of Margaret Street. The headquarters of his burgeoning empire was a block away at 201 William Street. Offices and inventory were sequestered here, and in the summer of 1986, Jimmy decided to install a “recording studio” in one of the corner offices on the 2nd floor overlooking the Gulf of Mexico.

Jimmy’s skills as a singer songwriter by this time had been well established. However, his business acumen, while certainly not lacking, was not a priority.

With that in mind, he had his business partner, Sunshine Smith in place, along with an experienced retail manager, an accountant, and me, a recent arrival in town to figure out how to best utilize a growing mailing list and a nascent mail order operation. A daunting task that I knew would require some research, and I wanted to do my best to impress.

Back story: I was a recent college graduate, married, father of two and thought my place in Margaritaville middle management was secure. This lofty opinion was put to the test one evening as I left the office, peaked in the corner studio to say so long to Jimmy. He gave me a wave and then asked, “Oh hey, would you run over to Turtle Kraals and get me a Barbancourt & Tonic?”

I wasn’t fully familiar with the responsibilities of a mail order manager, but I assumed fetching drinks for the boss was not one of them. I sighed, and what I guess was a classic eye-rolling fashion replied, “Yeah sure, I work for you, whatever you like.”

Jimmy sensed my sarcasm and not skipping a beat countered with, “You don’t work for me, you work with me. Now quit your bitchin’ and go get us a both a drink.” We had 2, and then 2 more and he, and this story, have been buying me drinks ever since. It was a pleasure and a helluva 3 decades.