Jim began his career in financial services as an attorney with the Federal Reserve Bank of New York, where he focused on a variety of regulatory issues and enforcement matters. He assisted with regulatory enforcement actions related to the Bank of Credit and Commerce International, as well as with several white-collar criminal prosecutions. Jim left the New York Fed to become General Counsel of Chicago Board Brokerage, a joint venture of the Chicago Board of Trade and inter-dealer broker Prebon Yamane, which was created to handle electronic trading and clearing of United States Treasury securities. He later joined Prebon, where he took responsibility for business planning and product management. Following Prebon's sale to Collin Stewart Tullett in 2004, Jim came to Promontory, initially as a Consultant.