Chamorro began his career as an industrial accountant before joining his family's textile business. Through business endeavors, he accumulated a massive personal fortune by investing in hotels, agriculture, media outlets, restaurants, insurance companies, banks, factories, construction companies, airlines, and car rentals.
From 1993 to 1994, Chamorro served as Vice-Mayor of Managua under Arnoldo Alemán and is credited with the modern city center's revitalization for his contribution toward its construction
In late June 1995, President Violeta Chamorro (no family relation) called upon Chamorro and a commission that worked alongside then Minister of Finance Jose Evenor Taboada Arana and representatives from the international private sector and financial services industry to create the 1996 Tax Law Reforms to stimulate investment
The reforms were eventually shelved after they prompted large protests organized by labor associations led by Victor Tirado Lopez
From early December 1997 to July 23, 1998, Chamorro briefly served as Vice president of Nicaragua and President of its National Assembly until his resignation stemming from corruption allegations which he would vehemently deny, later returning to his private sector projects.
