He earned a bachelor's degree from Washington and Jefferson College, graduating in 1976 with honors in political science and sociology.

He earned a master's degree from the School of Social Service Administration at the University of Chicago in 1979.

He worked as a reporter for the Martin Countian in Inez, Kentucky in 1980–81, and field coordinator for the Appalachian Alliance in 1982.

In December 1982 he became coordinator of the Kentucky Fair Tax Coalition (KFTC), which became Kentuckians For The Commonwealth in 1988.

In 2009, Szakos was arrested by his own health insurance company, Anthem Blue Cross, after he tried to ask why his organization's premiums had risen 14%.