Trip Bennett was born, raised, and educated in Texas. The nickname "Trip" was given because he was the third (triple) with the same namesake after his grandfather and father. In 1975, he married his wife, Alice, and graduated from Texas Tech University with a Bachelor of Architecture. After college, Trip and Alice began a family with two children, spending the first 8 years working for a variety of Architectural Firms in Texas and New Mexico. In 1983, Trip established his first Architectural practice with two other partners: Bennett, Lewis & Garcia in San Antonio. His initial focus here was primarily in adaptive renovation/restoration of historic structures and design of custom single family residencies. Due to a significant economic turn-down in Texas in the late eighties, Trip closed the practice and relocated his family to San Diego in 1989. Since then, Bennett has been fortunate to work in and around San Diego designing custom homes for individual clients. He is currently licensed and works in California, Utah, Texas, and Arizona. Bennett's architecture has been featured in numerous publications and received both regional and national design awards. In the recent past, he received the 10 News Leadership Award for leading the community effort to renovate Fire Station 13, conferred with the "Outstanding Rotarian of the Year" for the La Jolla Sunrise Rotary Club, and recognized as Best Architect in the La Jolla Light reader's poll as "Best Architect" in Ranch & Coast magazine.
Bennett's service to the community includes roles as President and current member of the La Jolla Sunrise Rotary Club, founding Board Member, and President of Ballet Arte Dance Theatre, Vice President of the La Jolla Historical Society Board of Directors, past Chairman of the La Jolla Concours d' Elegance, and until recently, served as the Interim Executive Director of the La Jolla Historical Society.