About me

My first visit to Key West was more of a last minute 8 hour adventure than a well planned trip. I had jumped onto a Halloween cruise with family and friends in Miami, with a stop in the Conch Republic early November of 2008. A local legend, Captain Tony Tarracino had passed away the day before.

I disembarked the ship and headed by myself down Duval street then ventured a bit south until I found Hemingway's house. The tour was everything I expected, although the tour guide seemed a bit irritated with me. Perhaps I should have let someone else answer his Hemingway trivia questions but I couldn't help myself.

The day trip was completed with shopping in Old Town, lunch at Sloppy Joe's and last minute beers at Hog's Breath Saloon. I embarked back onto the ship with a huge smile on my face. My life had just changed. I finally had an end plan.

Currently, I live on the historical eastside of Milwaukee with my beautiful girlfriend Kristin and my 9 year old son Cole. I met Krissy on St. Patrick's Day nearly 3 years ago and it's been a great ride ever since. She loves Key West almost as much as me. I've taken her twice and besides breaking her ankle on the first trip she totally loves the island.

Coco (say Cole twice in a row fast) has never been to Key West as he constantly reminds me. I'll get you there soon number one son, I promise. In the mean time he's playing soccer, baseball, basketball and contemplating a career in hip hop music.

There's been many variations of my nickname "Jake" over the years, most of them due to my last name. However, " Jakes the Legend" was bestowed upon me by Ken Jakalski, my old high school coach and a member of the Illinois Coaches Hall of Fame. Not only is he a great coach but the man has done more for the youth of America than anybody I've ever known. So, I proudly use his moniker for the blog with pride.

As mentioned, I'm a huge Hemingway fan, political historian, international investor, Chicago Sports enthusiast, avid art collector and my passion is the stock market. I grew up in Yorkville, Illinois in the heart of republican country. My favorite high school history teacher was Dennis Hastert who went on to become a long serving congressman and eventually Speaker of the House.

That being stated, I didn't leave the GOP as much as the GOP left me. It's been overcome by disgruntled old intolerant people living in a bubble desperately trying to hang onto a bygone era. Where change is bad, being poor is a crime and government is evil unless you need a road built. Talking heads have a book agenda and don't let facts get in the way of a good headline. The GOP is just no longer my cup of tea. No pun intended. But they remain my friends.

My purpose of this blog is mainly to entertain myself. I'm not on Facebook or Twitter. My current favorite person is the Dos Equis man (most interesting person in the world) and he's not even real! If it keeps my Key West aspirations focused and promotes the island in a positive way I'll be happy. If anyone else is entertained, likes the photos or finds my stock picks useful more power to you,

In the meantime, I'll dream of cocktails at Willie T's or dinner at Blue Heaven while I make plans for my next island adventure. Stay tuned.......

Next Stop Key West


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