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Island Investing

Riffs, rants, and the upside of investing from way off Wall Street


Island Investing: Now Almost Reaching Cuba

After a break for the holidays and the recent IIM annual meeting, my Island Investing column is back in the KeysWeekly. It’s now being published throughout the Lower Keys and Key West, too. The article below was in today’s paper.

Hello again, island investors! I’m happy to say my column is back on a regular schedule.

I’d like to pick up by introducing myself to new readers in Key West and the Lower Keys. Last year this column ran for six months in the Upper Keys Weekly and was originally intended to answer questions about investing. I planned to give away a free T-shirt to anyone who emailed a question, which I would then answer in my next column. As it turned out, however, I got no questions from anyone except my mother. Zero. Zilch. Bupkus.

Being the analytical type, though, I did not take it personally. There was a simple economic explanation obvious to anyone who has ever walked down Duval Street – there is already a staggering oversupply of cheap T-shirts being hawked in the Keys. Mine never had a chance.

That lack of questions turned into something even better than my original plan, though, because it gave me the flexibility to cover all sorts of topics. I wrote on everything from index funds to credit default swaps to inflation to psychological biases, and based on the comments I’d hear at Winn-Dixie, people seemed to enjoy it. So, next week I’ll start again.

Regarding my background – I am a portfolio manager at an independent firm I founded in 2008, Islamorada Investment Management. All I do is analyze stocks, I have zero ties to any Wall Street firms and all my family’s life savings are invested in the funds I manage. I cannot give advice on specific investments here, but I think I can help you learn how to think independently about investing. I’ve also taken a fiduciary oath, which among other things means that while my columns might be opinionated, they won’t be conflicted.

I have many opinions about the way Wall Street treats individual investors. As one of them, you really have two choices when it comes to your own financial future. You can either be a consumer of financial products, or you can learn to be a real investor.

This column is about the latter.

Cale Smith is the portfolio manager of the Tarpon Folio and Gecko Folio. His firm’s website is and his blog is