Paul M. Phipps entered the property & casualty insurance business on October 2, 1950, after working for two years as a life insurance underwriter with The Mutual Life Insurance Company of New York.

Paul Phipps, a graduate of Hopkinton High School, Class of 1939 and Holy Cross College, Worcester, MA, Class of 1943, served four years of active duty in the United States Marine Corps during World War II, in the Pacific operations, final rank Captain. Under the "G.I. Bill", he completed a graduate year at Babson Institute of Business Administration, now Babson College, Wellesley, MA.

In 1948, he joined the sales force of Mutual Life of New York. Paul Phipps, and his wife, Ruth, lived in Framingham, MA, working exclusively with Mutual of New York, until the opportunity to acquire the Wayne E. Hughes Insurance Agency, 80 Main Street, Hopkinton, MA., prompted him to establish his insurance business in Hopkinton.

As the town of Hopkinton continued to grow so too did the Phipps Agency. In 1975, Paul's son, Robert A. Phipps, joined the agency. Rob is a 1973 graduate of Susquehanna University, Selinsgrove, PA. After preliminary training within the agency, he completed courses at the Aetna Casualty & Surety Company Home Office School, Hartford, CT, The Mutual Institute of the Kemper Companies at Long Grove, Illinois(Chicago), and Oberlin College, OH. Rob went on to obtain the highly regarded Certified Insurance Counselor (C.I.C.) designation. Robert was elected Vice-President of the agency in 1980 and President in 1990.

The agency has always been an integral part of the Hopkinton community, with agency principals taking prominent roles and the agency a willing sponsor. Paul M. Phipps was a charter member of the Hopkinton Kiwanis Club, a past president and secretary; a founder of the Hopkinton Little League, a president of the League, and also a team manager for 15 years; Founder of the Hopkinton Chamber of Commerce and Chairman for three years; active in Boy Scouts, including fund raising; Chairman of most other fund drives, including Cancer, Heart & March of Dimes; member of Elmwood School building committee; Coach of CYO baseball teams and Chairman of St. John’s RC Church Finance Committee and fund Drive for new Parish Center.

Robert Phipps, Agency President, is a corporator of the Strata Bank in Hopkinton and served on the Board of Directors of the Hopkinton Education Foundation for four years. He was an active member of the Hopkinton Parks and Recreation Commission for 14 years and was also the chairman of the Town of Hopkinton Marathon Committee for 14 years. Rob was active in coaching Little League baseball and softball and Babe Ruth for 15 years and has been a member of the Hopkinton Lions Club since 1983. Rob was honored as Middlesex News Man of the Year in 1996

On June 19, 1989, Brian E. Thomas, Executive Vice President and a 1988 graduate of the University of Maine at Orono, joined the agency. He completed the Aetna Casualty & Surety Company Home Office School, Hartford, CT and went on to earn membership in the Society of Certified Insurance Counselors in November of 1992. Brian is a past board member of the Hopkinton Chamber of Commerce and the Hopkinton Community Endowment. He has coached little league, basketball and soccer. In April of 1996 Brian and Paul Phipps were inducted into the Hopkinton High School Athletic Hall of Fame. Brian, a life long resident of Hopkinton, continues to reside in town with his wife, Pam, and two daughters, Rebecca & Nicole.