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Frank Schilling, Entrepreneur, Cayman Islands

Frank Schilling is a Canadian-born entrepreneur, investor and property developer who has called the Cayman Islands home for more than 25 years. In this interview, he shares his perspective on Cayman’s evolution as a place to live and invest, the growth of its luxury property market, and his vision for major developments including Secret Beach in Grand Cayman and Port Zeus in Cayman Brac.

What originally brought you to the Cayman Islands?

Truthfully, taxes. I’m Canadian and had a young internet business that was growing but had not yet crossed a threshold for a prohibitive level of exit tax. My tax lawyer advised that if I left sooner rather than later, there would be a materially lower tax bill due.

I visited and researched several other island nations in the same hemisphere that offered a low taxation regime, and the Cayman Islands were far and away a more livable and welcoming alternative to any others. Even 25 years ago.

Why do you think so many people are looking at the Cayman Islands today as a place to live, invest and buy property?

When I first arrived here, I was shocked there were not more people like me with businesses like mine interested in operating from here. Even back then it was a very desirable place to build a life.

Over the past 25 years the Cayman Islands has become much more of a “place” and less of an island in the sun. There is very modern infrastructure here, incredible healthcare with five major hospitals and great practitioners from all over the world. The food is outstanding, and it’s just unlike other Caribbean islands. The Cayman Islands is the Monaco of the Caribbean.

What sets Cayman apart from other international destinations competing for the same investors and high-net-worth residents?

Your money is safe here. Private equity sized returns are possible with the security of real estate ownership. The small amount of required deposits on presales, which are part of the real estate and finance ecosystem, make the Cayman Islands a very desirable place to acquire a second home or put money to work.


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How have you seen Cayman change over the past 20 years, and where do you think the biggest opportunities are today?

Firstly, the Cayman Islands are safe, orderly and organized. There is security and rule of law. It’s a terrific spot to raise children with great education options. The healthcare and food infrastructure make Cayman a place where you can grow old and eat well.

The roads system is without question the best in the region and has really modernized. The growth of medical tourism has spun multiple hospitals and hundreds of service providers. It used to be that if I got sick in the Cayman Islands, I would go to Miami. Today, when I get sick, I come to the Cayman Islands because the care is better, even if you have the money to pay for the best healthcare anywhere.

You are developing Secret Beach in Grand Cayman. What did you see missing in the market, and what are today’s luxury buyers looking for?

I felt that there was a shortage of designer finished, tastefully built, and fully serviced oceanfront residences. We found the perfect rustic sandy beach within arms reach of Hotel Row and are building a sublime, limestone clad group of structures that feels like a neighborhood. Luxury amenities include a breathtaking oceanfront infinity pool, owner’s lounge and bar, on-call car and butler service, and an elaborate fitness concept with a Hamam spa, Finnish sauna, and TechnoGym Fitness workout machines. 

I’m building the high-end structures that I would live in myself. That drives me.

Secret Beach

You are also developing Port Zeus in Cayman Brac. What is your vision for the project, and why do you believe Cayman Brac has significant untapped potential?

Everyone in the World who has heard of the Cayman Islands understands there is more than one island.. But few realize that 99% of the population live in Grand Cayman, or that the Sister Islands are far removed from each other by 90 miles of water, or that they are in many ways more naturally beautiful than Grand Cayman.

Little Cayman is a biodiverse heritage zone and Cayman Brac is the breathtaking but hardscrabble place first discovered by Christopher Columbus in 1503. All the great merchant class and entrepreneurs and businessmen in these islands hail from Cayman Brac. Yet “The Brac” has largely been left behind with just several hundreds of residents because there is no natural safe harbor there.

As a Caymanian immigrant who has had 4 children in these islands, I feel it is a special duty and honor to own and work towards the first air-sea gateway in the Western Caribbean. The Port Zeus lands we own represent 120 acres, adjacent to the airport in Cayman Brac, which are designated on environmental maps as a “port zone.”

Port Zeus has a unique opportunity to be developed and to transform the life of Brackers and Caymanians in general. This project is immensely frustrating due to the lack of pace (which I do not singularly control), but I work on it each day and with the support of the government, I intend to see the job through in the next few years. My vision calls for creating connectivity and vibrant inter-island commerce that most outsiders are shocked do not already exist. My duty is to correct this wrinkle in the universe and give our nation’s motto: “He hath founded it on the Seas”, the dignified resonance it deserves. I love this project and my family and I are going to get it done.

Port Zeus

Cayman is well known as an international financial centre, but increasingly it is also becoming known for luxury real estate and lifestyle. Do you think the perception of Cayman internationally is changing?

Cayman made its name in the movies. Its cinematic perception was based in the reality of big banks during the 1980s, willing to take cash (wet or dry, by the suitcase or duffel bag) from anywhere without question.

That reputation spread but gradually started to die in the late 90s, ending with a coffin-nail in September of 2001 when rule of law triumphed over illicit funds in the wake of 9/11. Today Cayman is still British-governed, but the banks which built the Islands off-white reputation are gone.

Now, Cayman is a much more mainstream, US-centric place with integrity, rule of law and unassailable banking standards. This new reputation has attracted and intertwined significant parts of the US financial services sector.

In short, the Cayman Islands does the “doing” in global finance and makes the wheels turn. We are the servants of the financial system. We make it better and we make it hum, for everyone. Wealthier companies and people have followed, which has driven luxury real estate among other things.

What are some misconceptions international buyers and prospective residents have about living and investing in the Cayman Islands?

Cayman is a first world place. We are an open and welcoming society where one can come to invest, buy a home, live and make a life. Cayman is less of an island in the sun and more of a “place.” We have excellent food, infrastructure and healthcare. Life here is actually like something you dream about. The downsides are genuinely few here and the upsides overwhelmingly special. It is a unique place filled with well-minded and mannered people. Nearly every resident has a passport because of the requirements to live here, and we are all worldly travelers.

For someone considering moving to or investing in the Cayman Islands for the first time, what would you tell them?

Be sure to travel. The Cayman Islands are small. Just like living in New York and never leaving the upper Eastside or Soho, if you stay too long here without something to do or without going somewhere else, any crack in the sidewalk will eventually get on your nerves. Live and enjoy here and travel frequently. There are many destinations one door away, and when you return you will have a renewed appreciation for Cayman’s incredible lifestyle, healthcare, food and safety.

Frank Schilling is an entrepreneur, investor and property developer based in the Cayman Islands. Through projects including Secret Beach in Grand Cayman and Port Zeus in Cayman Brac, he is focused on creating high-quality residential, hospitality and infrastructure developments that reflect Cayman’s growth as a global destination for living, investing and doing business.