Real Estate Development: Through CVD, Settles specializes in real estate development where he transforms properties into desirable homes and commercial structures. CVD renovates them into beautifully unique properties that people are proud to call home. For more than 20 years, Settles has invested in many neighborhoods in Boston and throughout New England.

The Business Consulting arm of CVD focuses on hospitality and entertainment where creative visions are transformed into exceptional entertainment concepts. The one-of-a kind establishments, and events include the redesign of Boston’s historic Bob the Chef’s Restaurant into Bob’s Southern Bistro in 1997, and again in 2010 which today is the acclaimed southern inspired Darryl’s Corner Bar & Kitchen. In 2008, Settles was the founding member of the Beehive Restaurant and Bar in Boston (no current affiliation). He was the creator and founder of the international BeanTown Jazz Festival in 2001. This two-day music extravaganza boasts more than 70,000 visitors from across the city of Boston and national visitors each year. Operated since 2008 by the Berklee College of Music, this beloved event is Boston's largest block party, and generates millions of dollars in support of the local economy.

In 2014, Settles launched Boston Means Business (BMB) to ensure that Boston’s small and medium business enterprises are informed, and poised for the city’s economic growth.  It is a business forum designed to provide critical information to the enterprises and was hosted in partnership with the Massachusetts Convention Center Authority. BMB featured presentations about the Economic Landscape of Boston from leaders committed to the economic vitality of diverse businesses in the region. In 2015, after the second BMB Forum, Settles joined forces with a number of business, civic and community leaders where BMB was expanded into a broader business initiative called Freeze Frame Black Boston, a Black economic manifesto (or strategy), from which a Black Economic Council of Massachusetts and a Black Political Action Committee (PAC) has been established.