How To Invest

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Island Investing

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



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The Superior Math of Value Investing

I believe value investing is the only rational way to invest. It’s two scoops of common sense, a healthy dollop of skepticism and a commitment to ordering off-menu entrees. While a certain level of analytical ability is required, investing intelligently is not nearly as difficult as Wall Street would like you to believe – if […]

Create Your Own Convertible

I don’t mean building a car – see this guy to do that. I’m referring to a bond that can be converted into stock. Convertibles are hybrid securities with the features of both stocks and bonds. They usually have lower yields than regular bonds, but an owner receives the right to convert the bond to […]

Build Your Own Annuity. Please.

Annuities seem to be enjoying a resurgence lately, thanks to the bear market. That’s a shame. Many companies sell annuity products that are so costly in terms of fees and penalties that they seem better suited for funding the salesperson’s retirement than the investor’s. Amazingly, some agents even recommend buying annuities inside an IRA, meaning […]

Geek versus Tarpon

From a trip yesterday afternoon with good friend Captain Ted Wilson. Fantastic time, as usual. ‘Tis the time of year for tarpon in the Keys. Here’s a video of the above, another of the tarpon leaping, and Ted where he’s most at home. Also, from the bow of Ted’s skiff, running through the mangroves. Ted’s […]

Signs of Life in Keys’ Real Estate?

From the front lines of the housing bubble, and direct from the father of Cale in the Keys, here is an update on the Key West real estate market. Dad doesn’t know I posted this, but he’s been putting these reports out every month for ten years and he’s got quite a following among the […]

This Week’s Sign the Lunatics are Running the Asylum

Kiplinger’s reports that expense ratios for stock mutual funds are rising, despite a horrific year of performance for most funds. As described in the article, when assets in a fund fall below certain “breakpoints,” management fees as a percentage of assets increase. So it could very well be the case that you, my dear mutual […]

Ask the Geek: Deal or No Deal

Q. Can you help me win on that Deal or No Deal show? A. Yes, if winning means maximizing the amount of money you take home, not picking the right suitcases. Here is my advice: 

Forget about winning the million dollars. The odds say it just won’t happen. The object of the game should be […]

Welcome to Y’all Street

An update of our original video. More about Tarpon, Spoke Fund® and swimming naked.

Links of Interest

Read something interesting lately? Post it in the comments or send it in. Why I Fired my Broker. The intro says it all: “With his 401(k) in ruins, our correspondent visits investment gurus, hedge fund managers, and a freakish Arizona survivalist with one question in mind: How can the ordinary investor recover?” Sent in from […]

Ask the Geek: Bank Rescue Plan

Q. How is this bank rescue plan supposed to work? A.  The basic idea is that if the big banks can sell off their bad assets, they can function again. The banks have known this but can’t find any buyers. The government is bringing buyers to the table by sweetening the deal. In one part […]