[1] Growing up in a military family, Espero lived in Vallejo, California, Jacksonville, Florida, Athens, Georgia, Norfolk, Virginia, Oak Harbor, Washington, Guantanamo Bay, Cuba, Naples, Italy, and Yokosuka, Japan.

He worked in the finance and banking industry, property management, local home development, and the Coalition for a Drug Free Hawaiʻi.

A few years later in 1987, he entered politics, working with former mayor Frank Fasi and his administration as the executive secretary of the City and County of Honolulu Neighborhood Commission.

In December 1999, Espero was appointed to the Hawaiʻi State House of Representatives by Governor Ben Cayetano to fill the vacancy left by the resignation of then-representative Paul Oshiro.

[3] He had also served as the Majority Floor Leader and Chairman of the Committee on Public Safety, Intergovernmental and Military Affairs (PGM).