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Island Investing

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


Island Investing: Intro Column

This week I started writing a new column called “Island Investing” for the Keys Weekly paper. It will be in the version that’s distributed in Homestead, Key Largo, Tavernier and Islamorada. Here’s my intro, out today.

Island Investing
Cale Smith
June 6, 2009

I’d like to use this column to answer questions about investing.

I am a portfolio manager at an independent firm I founded last year, Islamorada Investment Management. We have zero ties to any Wall Street firms. I also have no shortage of opinions about the financial advice that is typically given to individual investors.

It seems appropriate to begin by clarifying my beliefs about two areas:

1 – Wall Street exists to sell financial products. Many of the products sold to individual investors are just plain lousy. Financial consumers can either continue to buy inferior products or learn to shop smarter.

2 – You do not need Wall Street to invest successfully. In fact, you may be better off without it.

I’m exclusively focused on managing two portfolios, and then only in a pretty particular kind of way. So when people ask me about the world of finance, I’d like this column to help provide those answers.

One of the many things I love about the Keys is that it seems like everybody either owns or works at a small business. I believe that small business owners and operators – not the geniuses on Wall Street – make the best long-term investors.

I also think it’s unique that everyone in the Keys sincerely looks out for each other. I’ll consider this column a success if I can help a few independent investors and protect some others.

While I cannot give advice on specific investments here, I can help you learn how to think independently about investing. You should also know that my firm is a “fee-only” shop and a member of an organization called NAPFA. That means we cannot earn any compensation from commissions, referrals or selling financial products. So my answers to your questions may be opinionated, but they won’t be conflicted.

I have been warned by columnists in other papers not to expect too many questions. To that I say, “Harumph. We’ve got free T-shirts.” So pick a question about investing or Wall Street and send it to csmith (at) along with your shirt size. We’ll start from there next week.

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