My Encounter With Jimmy?Buffett ??

The world lost a legend last week with the passing of Jimmy Buffett.?

For those unaware of who Jimmy Buffett is, here are a few reasons why he was famous:

Music: Jimmy Buffett is primarily known as a musician, singer, and songwriter. He is best known for his unique blend of folk, country, rock, and Caribbean music, often referred to as “Gulf and Western” or “tropical rock.” Some of his most popular songs include “Margaritaville,” “Cheeseburger in Paradise,” “Fins,” and “Changes in Latitudes, Changes in Attitudes.” His music often celebrates a laid-back, beach and island lifestyle, and he has a dedicated fan base known as “Parrotheads.” I remember as a kid growing up how ecstatic my parents and their friends would be when Jimmy was coming to town. It was almost as if he had a cult-like following… if you consider a cult an entire generation of people.?

Margaritaville Brand: Jimmy Buffett is also famous for the Margaritaville brand, which includes restaurants, hotels, resorts, and a wide range of merchandise. Margaritaville establishments often feature tropical themes, live music, and a relaxed atmosphere. The brand is synonymous with the carefree, beach-inspired lifestyle portrayed in Buffett’s music.

Lifestyle and Persona: Jimmy Buffett has cultivated a public persona that embodies a carefree and beach-loving lifestyle. He’s often associated with flip-flops, Hawaiian shirts, and a laid-back attitude. This persona has made him a cultural icon for those who embrace the idea of escaping to a tropical paradise and living life with a sense of fun and relaxation.

Now that you know who Jimmy Buffett is, it’s time for me to tell my story about Jimmy Buffett.?

For those who don’t know me, I am an entrepreneur.?

One of the first companies I started was while I was getting my Entrepreneurship MBA at Babson College in Boston.?

My friends and I were aiming to create a company that represented the carefree lifestyle that we were currently living.?

So we started designing some crazy-looking Hawaiian shirts and named the company Fielder’s Derby.?

Although Fielder’s Derby no longer exists, (I will save that story for another day) there was a moment where we almost had Jimmy Buffett...

Given our brand’s persona and lifestyle were similar to that of Jimmy Buffett’s and our name was created from the Kentucky Derby we decided to make a BOLD move.?

We decided we were going to launch a Kickstarter campaign that would bring Jimmy Buffett to play at the University of Louisville’s football stadium the night before the Kentucky Derby.?

This idea was both insane and awesome.?

We created the campaign, got in touch with Louisville to rent out their stadium, and even got in contact with Jimmy’s rep to see if he was free and if he would be willing to do it.?

Everything checked out.?

The stadium was available. ?

Jimmy was free and liked the idea. ?

But the only problem was we had no money. ?

Similar to how in real estate you might have over 7 figures in pursuit costs before you actually close a deal, locking in the venue and Jimmy was north of 7 figures.?

The youthful 20-somethings that we were, wanted to throw caution to the wind and go all in to make this dream a reality.???

But the logical entrepreneurs that we were, knew that this was far TOO BIG a bet to take for such an early-stage company.?

Sadly we ended up canceling our campaign and with that our opportunity to meet a man who inspired us to create our company in the first place.?

I am now stuck living with the what-ifs of this story.?

Should we have done it?

Did we make the right decision to cancel?

What would you have done?

...

RIP Jimmy enjoy your Cheeseburger in Paradise.?

About the Author:

Dan Cosgrove is a partner at Anthem Capital.

Dan is a native of Cincinnati and is based out of Boston with his wonderful wife, cute baby, and a dumb dog named Waffles.

He is an entrepreneur and real estate investor who would love to connect to see how he can add value and joy to your life.