Rolston Anglin is the 28-year-old son of Clovena and McClurn Anglin and grew up in North West Point. He attended John A. Cumber Primary School, the Cayman Islands Middle School and Cayman Islands High School. He then went on to attend Sixth Form there. Rolston excelled academically and was consistently at the top of his classes during his primary and secondary education. This continued, as he would later graduate with honours from university.

Upon successful completion of three "A" levels, Rolston received a scholarship from the major international Accounting firm, Price Waterhouse, to attend university. While at University he was a member of the Phi Kappa Phi Honour Society and the Golden Key Honour Society. He graduated with honours from the Ohio State University. He then returned home to Cayman and shortly thereafter passed the Certified Public Accountant examinations on his first attempt. Price Waterhouse then sent him to work in the world's financial capital, New York City in order that he might gain additional exposure in the financial services industry. He worked with clients such as Morgan Stanley Dean Witter, New York Life Insurance Company, Windward Capital Partners, Permal Asset Managers and Deutsche Bank. This has allowed Rolston to become a well-rounded professional accountant with intimate knowledge of the products and services in the financial services industry.

Rolston and his wife Shena are active members of the Boatswain Bay Presbyterian Church and also work as the church's youth group leaders. This effort is driven by their desire to help guide and mold the young people in our district into becoming law-abiding and positive thinking citizens of our country. More recently, Rolston has also been elected as the Chairman of the Cayman Islands Christian Youth Workers Association in which he is working actively to co-ordinate the efforts of Christian Youth Workers Nationally.