[citation needed] He was the chairman and chief executive officer of Arvida Corporation[1][2] and Disney Development Company during the 1970s and 1980s.
Prior to this, he was the chief operating officer and a director of Penn Central Transportation Corporation, a multi-industry company that had approximately 40,000 employees.
Earlier, he was an investment manager with Dodge & Cox and the chief executive officer of subsidiaries at Kaiser Aluminum.
Cobb also serves on the Board and the Investment Committee for the Florida State Board of Administration, University of Miami, Woodrow Wilson International Center for Scholars, Eisenhower Fellowships,[9] Orange Bowl Committee, Council of American Ambassadors[10] and Cobb Family Foundation.
Other civic boards and memberships include Plymouth Congregational Church, The American-Scandinavian Foundation, the Icelandic-American Chamber of Commerce, Orange Bowl Committee, Council on Foreign Relations, the Urban Land Institute, and the Lincoln Institute of Land Policy.