Rolle grew up in the composed settlement of Holmes Rock, Grand Bahama; where he attended the primary school there under the tutelage of his grandfather and ‘great educator’ – the late Walter P. He then moved on to the Eight Mile Rock High school where he was a very active student having been co-captain of the undefeated senior boys basketball team in 1985, the year he graduated, having also serve
as Deputy Head Boy among other leadership positions there. Through both athletic and academic scholarships, Roger was able to matriculate to Bethune-Cookman College (now University), Daytona Beach, Florida, where he also held numerous positions of leadership; including that of the President of the Federation of Bahamian Students. He completed studies at this institution in April of 1989 with a Bachelor of Science degree in Accounting. Poised to achieve more, he completed graduate studies - having attained a Masters Degree in Business Administration (MBA) - at the level of Magna Cum Laude (the same as with his undergraduate studies) from Nova Southeastern University in Fort Lauderdale, Florida - in June 1993. Roger started out his career with a short stay at both Sun World Travel & Tours and Company Management Freeport Limited. He spent four (4) years each with the Bahamas Immigration Department and Island Project Company Limited with a brief period in between with the Grand Bahama Island Tourism (Promotion) Board - as Manager of Finance & Administration - in 1995/1996. As a result of the wealth of knowledge gathered in his previous job experiences to go along with an assertive work attitude, Roger then confidently established his own business (along with former partner Ralph Hepburn) in February 1998. This unique consulting firmed - Rags To Riches Consulting Company Limited (where he is the President and CEO) - is designed to help people start and maintain enterprise through exceptional but simple practices; and where an intrinsic passion abounds for dreams to become reality and where Rags can turn into Riches. This man has played a very active role in civil society including, charter president of the Holmes Rock Toastmaster Club (1625), treasurer of the Holmes Rock Youth & Sports Association. He is the former treasurer and director with the Grand Bahama Chamber of Commerce and is a charter member and treasurer of the Grand Bahama Chapter of the Alpha Phi Alpha, Fraternity, Inc. From a church perspective he serves as a Lay Minister and Senior Choir Director of St. Mary Magdalene Parish in West End and was also the treasurer there from January 2000 to July 2010. He has also served as a member on the Anglican Diocese of the Bahamas and the Turks & Caicos Islands - Finance Committee. His understanding of the importance of family makes him proud to be married to the fun-loving and energetic Lady Caroline Adderley-Rolle of West End (since 25th March 1995) and they have two children, Rashae and Rashad.