How To Invest

Want to know more?

Find out more arrow-white

Island Investing

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


Who We Are

Managing Partner and Portfolio Manager Cale Smith

The portfolio manager for the Tarpon and Gecko Folios is Cale Smith, the managing partner of Islamorada Investment Management.

Cale founded Islamorada Investment Management and created the Spoke Fund® model of portfolio management in 2008. Prior to starting IIM, Cale served as the managing director of an investor relations firm, the director of research at an independent research firm, and the lead equity analyst for an independent research firm near Washington, D.C. He also served as an analyst at a hedge fund. Cale is an honors graduate of the U.S. Coast Guard Academy, where he majored in business management. He received an MBA from the College of William & Mary. In 2000, Cale competed in the Olympic rowing trials as a single sculler.

Cale is also Treasurer on the Board of Directors of the Florida Keys Electric Cooperative. He is a director on the operating board of Mariners Hospital and is on the investment committee for Baptist Health South Florida, which oversees $3.0 billion in assets.

Cale previously served as President of the Islamorada Chamber of Commerce and in 2013 was presented with the Irving Eyster Award for outstanding volunteer service to the community.

Please scroll down to read a letter from Cale.

To contact Cale, call (305) 522-1333 or email csmith at

Partner and International Portfolio Manager Lauretta Reeves, CFA, AWMA

Lauretta “Retz” Ann Reeves is the international equities portfolio manager and a wealth management advisor at Islamorada Investment Management (IIM). Ms. Reeves joined IIM in 2013. She has served as a portfolio manager and Co-Chief Investment Officer of the Value Strategy at Hansberger Global Investors (HGI). Before HGI, Ms. Reeves was a portfolio manager and Senior Vice President with Franklin Templeton Investments.

Ms. Reeves is a CFA® Charter Holder and a member of the CFA Institute, where she is a member of the Practice Analysis Working Body, The CFA Society of North Carolina, and the Business and Professional Women/Triangle. She holds the designation of Accredited Wealth Management Advisor (SM) (AWMA®) from the College of Financial Planning. She received a BBA from Florida International University with High Honors and an MBA from Nova Southeastern University.

To contact Retz, call (954) 907-2664 or email lreeves at

A Letter from Founder Cale Smith

I’m Cale Smith, the founder of Islamorada Investment Management and portfolio manager for the Tarpon and Gecko Folios.

We are a value investing firm located in the village of Islamorada in the Florida Keys.

Islamorada is pronounced aisle-a-more-AH-dah. The ‘s’ is silent and it means “purple isle.” The odds are good that no matter what time of year you’re reading this, its sunny and beautiful here. My apologies, Chicago.

We named our first portfolio after a fish. Our first email newsletter was called “Spinach in a World of Chocolate.” Our first slogan was, “One geek in the Keys is worth two suits in the city.” So although we’re good at what we do, we don’t take ourselves too seriously.

Think Warren Buffett meets Jimmy Buffett.

We manage the investment portfolios of friends here in the Keys and up north using a value investing philosophy. That means we view buying a stock as purchasing a long-term partial ownership position in a business, not as a piece of paper that changes hands daily. We build focused portfolios of 15 to 20 meaningful positions in the common stocks of good businesses run by managers we admire.

We do our own research, keep transactions costs low, buy for the long-term and above all ensure we buy shares when they are cheap. We are solely concerned with getting a good price on the shares of a few great businesses – independent of economic forecasts, Wall Street consensus and noise in the financial media.

The Tarpon Folio was built for long-term growth, and I have invested just about all of my family’s life savings in it. The Gecko Folio is a high yield fund built by special request for investors seeking monthly income. I have invested my own capital alongside our investors there, too.

We are a fee-only firm, meaning we don’t get paid through commissions or referrals like most Wall Street firms. We’re not brokers and we don’t provide advice, sell anyone else’s products nor pay much attention to Wall Street. We like to think our mission is to save investors from mutual funds.

We also manage money a little differently than you may be used to. Both portfolios I run were built differently than the “pooled” model of mutual funds and hedge funds. We call our approach a hub and spoke model, or Spoke Fund® for short.

Imagine a first grader drawing a picture of the solar system. The sun is the hub – my own family’s money, in this case – and the spokes lead to all the planets, which are our investors’ accounts. Any trades in the core portfolio are executed simultaneously across everyone’s account, and all accounts are securely held and fully insured by an independent third party company that gives all of our investors 24/7 online and phone access to their accounts.

In short, we’re all in it together. I’m a former hedge fund guy. Lauretta is a former mutual fund gal. We both believe Spoke Funds are better.

Our investors all share a common belief that traditional investment services are not working in their interest. They are smart, professional people who have a sense of humor, respect a good work ethic and have some humility. Each of our investors is an expert at something, just not analyzing public companies.

Some of our clients are very wealthy, and some are not – but those who are well-off tend to like that we are accessible to everyone. So, our customers have pretty inclusive attitudes. Also, 84% of our investors wear flip-flops every day.

We’re always looking for new investors, but we may not be for everyone. If you want Ivy League resumes, mahogany desks or a range of different financial services, you’d probably be better off working with a more traditional firm.

If you want good results at a low cost and an occasional margarita with friends, however, then we might be the place for you.

So please check out our site, and contact me anytime if you’d like to talk further.

—Cale Smith