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Island Investing

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


Who We Are

Cale Smith, Managing Partner

Cale is the founder and managing partner of Islamorada Investment Management (IIM), and manages an energy fund called the Tarpon Folio.

In 2008, Cale founded IIM and created the Spoke Fund® model of portfolio management. Prior to IIM, Cale served as the managing director of an investor relations firm, the director of research at an independent equity research firm, and the lead equity analyst for an independent research firm near Washington, D.C. He was previously an analyst at a hedge fund, a project manager at the world’s first commercial internet service provider, and ran business development at an RF engineering firm.

Cale is also Treasurer on the Board of Directors of the Florida Keys Electric Cooperative, which provides electricity to approximately 30,000 members in the Upper Florida Keys. He is a director on the operating board of Mariners Hospital and previously served as President of the Islamorada Chamber of Commerce and was a recipient of the Irving Eyster Award for outstanding volunteer service to the community.

Cale is a veteran and an honors graduate of the U.S. Coast Guard Academy. He received an MBA from the College of William & Mary. In 2000, Cale competed in the Olympic rowing trials as a single sculler.

Please scroll down to read a letter Cale wrote to prospective IIM clients. To contact Cale, please 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

Thank you for stopping by.

IIM is 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 liquid net worth in it. The Gecko Folio, which I also manage, is an equity income fund built to produce sustainable dividends. For some time now, both portfolios have been invested exclusively in American energy companies.

IIM is a fee-only firm, meaning we don’t get paid through commissions or referrals like bigger 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. And in short, 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 happy to work with 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. Thx again for stopping by.

— Cale

Director of Financial Planning Jeffrey Alderfer, CFP®

A native of Harleysville PA, Jeffrey Alderfer earned a Bachelor of Science degree in Aeronautical Engineering from the US Air Force Academy, and a Master of Science in Systems Management from the University of Southern California. After serving more than twenty years as an active-duty Air Force pilot, he returned to Pennsylvania where he earned the Certified Financial Planner credential and founded Alderfer Financial Planning LLC in Wyomissing, PA.

After the events of 9/11/2001, Jeff volunteered to return to the cockpit with the US Air Force Reserve, and in 2003 he completed an extended tour of duty in the Middle East flying combat missions supporting our troops in Afghanistan and Iraq. Returning again to civilian life, he continued to serve part-time in the Air Force Reserve, retiring (for the second time) in 2009 at the rank of Colonel.

During this time, Alderfer Financial Planning continued to grow, eventually becoming Convergent Financial Strategies LLC, where he served as the Director of Financial Planning. In 2016 Jeff accepted a buy-out offer from his two partners, and subsequently began teaching personal finance as an adjunct professor at Temple University, which continues to this day. In 2023, Jeff joined Islamorada Investment Management where he oversees financial planning services and firm operations.

In his spare time, Jeff enjoys trail running, riding his BMW R9T, and spending time with his wife Alix and daughter Amy.