Let me say from the beginning, I am a Jimmy Buffett fan. I have liked his music since college and have been to, probably, 10 of his concerts. As I have told my daughters, his music just takes me to a place with a smile on my face and a drink in my hand…no matter where I am.

But on my way to work the other day, listening to Tin Cup Chalice, it occurred to me that Jimmy has a lot to teach entrepreneurs and content creators if we are willing to listen.

Create a Niche: When Jimmy Buffett came to Nashville those many years ago, it seemed nobody wanted him. He didn’t look like a country singer. In those days, he didn’t sound like a country singer. But he stayed willing to sound like “Jimmy Buffett.” Over time, he created a niche audience that wanted to hear the island sound at One Particular Harbor. Once he created it, that audience has loyally followed him for years!  Lesson:  Don’t wait for someone to choose you.  Create the audience yourself.

Have Fun With It: If you have ever listened to a Jimmy Buffett song, you know he talks about Changing his Latitude and his Attitude. His audience buys in. One time at a jam-packed concert (in the beer line) I accidentally bumped into another guy, spilling his drink. I quickly turned to apologize (that sort of thing can get you punched at many concerts). The guy said, “It’s cool! You are at a Jimmy concert!” Jimmy oozes a fun laid-back attitude…and people respond.  Lesson:  If you have fun with what you are doing, your audience will too…and they will love you for it.

Don’t Focus on Your Weaknesses: Though I am a big fan, I certainly can recognize that Jimmy Buffett is not the best singer or best guitar player. I am sure there are times you feel the same way about being a content creator. There are better writers. But don’t let that stop you. Had he worried about his weaknesses, he might never have moved to Key West in the first place. Bet on your strengths and put out your best, consistently. Soon, like Jimmy, you will be playing for a packed house.  Lesson:  Don’t let your weaknesses stop you from telling your story!

 Age Is Just a Number: Every year I hear a rumor that “this tour” will be Jimmy’s last. But every year, he keeps traveling the country to entertain his fans. Too many of us want to work hard so they can retire. If you love what you do, keep rocking as long as you want!  Lesson:  Keeping rocking and doing your thing as long as you want!

Nail Your Core…Then who knows? For years, Jimmy Buffett was “just” an entertainer. He had some songs like Margaritaville that were popular and he played concerts around the country. But somewhere along the way, his music became a way of life. Recognizing this, Jimmy built a restaurant and bar called “Cheeseburger in Paradise.” Now he has huge restaurants, casinos and even brews his own beer. He nailed his core and then built his brand from there. Jimmy started as an entertainer, but has built himself into a true entrepreneur.  Lesson:  Do what you do best…then keep your eyes open for opportunities along the way!

So let’s take a lesson from Jimmy and work hard at having fun. By taking his lead, maybe we can create the next iconic brand…and spend some time in Key West too!

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