Waldman was born in Washington, D.C. and attended the University of Connecticut for a few years before moving to Florida in 1977 transferring to the University of Florida in 1978, where he graduated with a degree in finance in 1980. Following this, he attended the Shepard Broad Law Center at Nova Southeastern University, graduating with his Juris Doctor in 1985. Waldman worked in private practice as an attorney and eventually rose to become the general counsel of Keiser University. In 1993, Waldman was elected to the Coconut Creek City Commission.