(See Part 1 here for the beginning of the story) As a “numbers guy” my mind was reeling with all of the opportunity that Captain Herman was tapping in to. On an island where there is a massive separation between the billionaires with virtually unused luxury vacation homes and the local population working diligently in resorts to serve tourists, Captain Herman was choosing a different path. His accent gave away that he was not from the Cayman Islands originally, but hailed from the nearby island of Jamaica. I was curious about this and even though our dinner was now ready, I asked one last question, “Captain Herman, you seem like the kind of guy that sees opportunity everywhere. To what end are you working so hard here in the Cayman Islands?”

The captain then told me about the large disparity in income for Jamaicans working in Jamaica and working in the Cayman Islands. In the Cayman Islands they can make almost twice what they would at home. With only a 45-minute flight between the two, many Jamaicans make the trip to the Cayman Islands. But Captain Herman’s heart and much of his family is still in Jamaica. With the proceeds from his farming, fishing, and restaurant business in the Cayman Islands, he’s building a small shopping center and a large guest house in Jamaica. The final chapter for Captain Herman will be a return home to enjoy time with family and friends paid for by his real estate investments.

By this time, dinner was ready and the kids were hungry, so our conversation ended. The Captain was gone when we finished dinner, so the rest of my questions will remain unanswered. Reflecting back on my conversations with Captain Herman, I picked up lessons to learn from this Jamaican entrepreneur. Parts 3 and 4 will detail what I learned.