He attended Robbins Preparatoy School in Connecticut and Eastman Business College in New York.
Bentley was the founding dean of the Boston YMCA School of Commerce and Finance which became a department of Northeastern University.
Bentley was then appointed a professor of accounting at Boston University's School of Business Administration.
He then resigned from this professorship and started Bentley College after many of his BU students wished him to continue to teach them.
Bentley was a supporter of various American artists and was interested in running, baseball, horseback riding, and wrestling.