David lives in Madison, WI with his wife, Monique. They met in his senior year high school English class. They have two sons, Jacob & Ben and two yellow labs (Bella & Oliver).

David graduated from UW-Madison with a degree in Risk Management. He is a third generation of American Family agents. His grandfather founded the home office agency ‘Wittwer, Kalbskopf and Webster’ in 1933. David’s dad, Chuck Webster, was an agent from 1954 to 1998. Degree's and Certifications: - BBA Risk Management (UW-Madison) - FSCP - LUTCF

David enjoys playing tennis (USTA), traveling, watching his children play sports, attending concerts/shows at the Overture Center and spending time with family.

David’s successes as an agent include multiple awards and recognitions: -26 All Americans -11 Line Leader Conferences -18 Commercial Line Gold Keys -7 Company Agency of the Month Awards -Company Life Record in 2001 & 2008 -State Agent of the Year for B&A 2017, 2018 & 2019.

Highpoint Estates HOA- Past President, Past President Waisman Center Friends Board, Rotary of Madison- Downtown