What You Can Learn From The Cayman Islands’ Path To Growth

Three days are too few to fully unwind into what makes the Cayman Islands special. Lobster at the waterside cafe, sparkling blue water lapping white sand, genuinely nice people living in a safe country that feels, well, just happy. I was there to teach a two-day Outthinker course for a local university, training fast-rising government officials on how to sharpen their strategic and innovative thinking skills.

At around $55,000, the Cayman Islands has one of the highest GDPs per capital in the Caribbean. By contrast, the Bahamas has a GDP per capita of about $20,000, and Guyana’s is one of the lowest at $3700.

Analyzing how the Cayman Islands got there shows that a core business principle can apply to nations too: delicately design an elegant customer journey and you will grow and grow and grow. What is your customer journey?

Here is how the Cayman Islands does it.


Every year about 1.5 million cruise-ship customers off-board at Cayman for a day. They don’t spend much, only $90 per person on average, but Cayman doesn’t need them to … yet.


Having fallen in love with the islands, many cruisers return for a family vacation. Every year about 400,000 visitors fly into the islands, family in tow. They spend about a week there, spending $1,000 on average. Cayman has just turned a $90 visit into a $7,000 trip … but they are not done yet.


Sometime during their week-long vacation, someone will approach the family with a question like, “You seem to be enjoying yourself so much – why not come back every year?” Visitors buy a waterfront condo, at just over $1M, and rent it out during the weeks they are not there. For a few years, the families return and their kids have fun scuba diving, kite-surfing, or kicking up sand. But as the kids grow older they are less intrigued by vacationing with their now empty-nester parents, and the parents start thinking about something new … taxes.


Stepping off my plane at the Grand Cayman airport, I saw three lines: visitors, residents, and citizens. I queued behind maybe 100 visitors and watched enviously as a few residents strolled confidently toward the front, having to wait behind no more than five people. Residence has perks and not just shorter lines, but taxes. Well known as a tax-efficient territory, the Cayman Islands is filled with tax planners, trust and estates experts, and accountants to help you (legally of course) protect your hard-earned assets against the grabby hands of the IRS. Foreign residents might invest $1M, $5M, or even more with the Cayman Islands.

Crafting a lifetime journey

By carefully evolving a customer journey that leads a $90, one-day cruise vacationer patiently toward a major resident investor, the Cayman has grown a jewel of prosperity out of a swath of sand in the middle of the Caribbean. Imagine what a well-thought-through lifetime customer journey could do for you.

Here is how to craft your lifetime journey:

  1. Identify a few of your most valuable, loyal customers and analyze how they came to be. How did they first engage? What did they do next? What were the key steps along the way? The Cayman might have, for example, interviewed their five wealthiest expat residents.
  2. Look for a common path. Not every Caymanian resident arrives at the Cayman as a home the same way, but if you look at enough paths, some patterns will start to appear. Eventually you build a prototypical story about your ideal customer. For example, the Cayman’s interviews might have revealed that most of their wealthy expats first visited through a cruise-ship stop.
  3. Develop the narrative. Having developed your prototypical story, think through the story’s twists and turns, the emotional ups and downs, the fears and hopes that keep the customer along their journey. The Cayman analyses would eventually reveal the journey outlined above – from cruise to vacation to ownership to residency – and at each point there are hopes (time with my family!) and fears (they are going to tax away my hard-earned income!) that keep the “customer” coming back.
  4. Identify the key touch-points. That emotional journey will reveal the critical touch-points that must be there to keep your customers flowing. Without those touch-points, you will allow a leak to form in your funnel and you will fail to reach your full potential.

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