Jamie earned his MBA in Finance and Information Technology from the UT Graduate School of Business. His BA is a dual degree in Russian Studies and International Relations from the University of Wisconsin.

He lived in Moscow for three years, where he was involved with several start-ups ranging from videoconferencing services to donuts. Following that, Jamie returned to his native Boston and managed a consumer products distribution company for three years. Owning his own small business as an independent business consultant, he served several small business clients.

Jamie has also worked for Dragon Systems, E! Entertainment, and Dell computer in various sales and consulting capacities. He worked at USWeb/CKS (later marchFIRST) as an Internet strategist, and was recognized twice for his excellent analyses and customer relations.