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Bennett Bernstein has been working in the industry since 1988. Bennett's first job was as a Producer/Asst. Sr. Producer at WWDB-FM in 1988. Bennett then moved on to Boston Package Delivery in 1994 as a Delivery Driver. In 1993, they became a Senior Sales Representative/School Coordinator at Atlas Creatives, Inc. In 1996, they were promoted to Vice-President/President in at Atlas Package Delivery, Inc. In 2006, they worked as a Driver Recruiter at Dynamex, and in 2008 they became a DJ at Monster Mini-Golf. In 2010, they began working at RTD Logistics as an Operations Compliance Manager and later as a Compliance/Operations Manager. Bennett also currently owns BBthe DJ.

Bennett Bernstein attended Temple University from 1984 to 1988, earning a BA in Radio-Televison-Film and a Bachelor's degree in Radio and Television. In 2015, they obtained a TSA certification from Homeland Security Careers.