In 2001, Webb co-founded The Barbarian Group, an award-winning digital ad agency. He served as its COO for the first ten years of the company's existence. Webb left in 2011 to pursue angel investing in, and writing on, technology and advertising. He is an angel investor in Foursquare, Circa, Percolate, Sherpaa, Nestio and Timehop. He is an advisor to several other tech startups and marketing services companies, including Hard Candy Shell, and Small Girls PR.
Webb is author of Agency: Starting a Creative Firm in the Age of Digital Marketing, released by Palgrave Macmillan in 2015, and an avid writer on technology, advertising, economics, and government. He graduated from Boston University with a degree in International Economics in 1992. He serves a board member of the VCU Brandcenter, one of the most renowned advertising graduate schools, and was named as Creativity Magazine's 50 most creative people in marketing (2008). He was born and raised in Fairbanks, Alaska.