After attending New Trier High School and Ithaca College where he received a BA, James started his career with Drexel Burnham Lambert then Rodman & Renshaw ultimately becoming a Member of the Chicago Board of Trade.

While actively trading commodities, James purchased, operated and eventually sold a restaurant parts and supply business.  He also took an active role in retail property management where he was personally responsible for a large portfolio of retail shopping centers.  In addition during the same time period, James designed, patented and manufactured medical garments, two of which are still sold internationally today.