Not long after graduating from Stafford Senior High School in 1983, he started working for Stride Rite, and where he became a regional vice president at the age of 25.

Later, he managed growth and development in the occupational footwear market with Nautilus, Skidbuster, Third Watch, and Avenger.

[6] He also worked at EJ Footwear LLC (formerly known as the Endicott Johnson Corporation), Iron Age and Lake of the Woods.

[9] In 2004 Elsey founded Soles4Souls, a nonprofit organization that sends shoes to recovering communities struck by natural disasters.

[10][11] Soles4Souls became one of the USA's fastest growing charities,[12] but faced criticism over claims that a $1 donation would provide a pair of shoes to someone in need, since the used shoes they received were resold to wholesalers that then sold them to small businesses in developing countries instead of directly shipping them abroad.