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Island Investing

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


Category: For Investors

Island Investing: Reducing Risk

This week’s column for the Keys Weekly. Island Investing Cale Smith June 13, 2009 I received three questions from readers of last week’s column. I’m happy to say two of them were from people other than my mom. Don’t forget: free T-shirt. Send your investing question to csmith (at) If nothing else, you can […]

Tarpon Folio Letter to Investors – May ’09

Here’s my firm’s latest letter to investors in the Tarpon Folio. To receive these, sign up here. In This Issue Cale’s Notes: A new look for IIM. Portfolio Summary: Up 13% in May, up 59% since launch. Value Investing 101:  Competitive strategy, simplified. Get To Know Your Company: Crazy for CarMax. Ask the Geek: Big […]

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 […]

Book Notes: Spend ‘Til The End, Part 2

Notes from the second part of Spend ‘Til The End. Here’s what this is all about, and last week’s notes. Read Kirk’s comments on last week’s post for some thoughts from a fee-only advisor, too. Part 2: Financial Pathology Here’s how I would summarize this section on Twitter: “Wall Street has your worst interests at […]

Book Notes: Spend ‘Til The End, Part I

As mentioned previously, some notes from Spend ’til The End. Part I: Smooth Financial Plans There are three parts to an economics-based approach to financial planning: 1 – Maximizing your spending power. Making financial choices that provide you with more money to spend for the same effort. For instance, whether to collect a smaller Social […]

Book Notes: Spend ’til The End, Intro

“If you continue to do what you’ve always done, you’ll continue to get what you’ve always got.” – Yogi Berra My firm provides only a small sliver of the entire spectrum of financial services. We manage two portfolios, and only in a pretty particular kind of way. So when friends and family started coming to […]

Links of Interest

Waiting for CNBC. Desperately seeking adult supervision. The Fed’s Trillion. An amazing graphic. Everything You Ever Really Wanted to Know About Personal Finance on Just One Page. Free ebook. Making It. Warren Buffett, Malcolm Gladwell and why talent is overrated. Musings from the Berkshire Hathaway meeting. Charlie Munger: “As I move close to the edge […]

Why I Built a Spoke Fund®

A year ago I was struggling to solve a challenging problem. After years of dreaming, I was finally going to start my own investment fund. The problem, though, was choosing the kind of fund I wanted to run. I wanted to build a firm that was independent of Wall Street, so I could manage my […]

What is a Spoke Fund® ?

A Spoke Fund® is a group of separate investor accounts linked to a portfolio containing most of the liquid net worth of that fund’s manager. “Spoke Fund®” is short for “hub and spoke” model. The portfolio manager’s money is the hub and the spokes lead to each investor’s account. Any changes in the hub are […]

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 […]