Steven Rupert has attended over 4,000 mediations since starting with Allstate Insurance in the mid 1980s, handling litigation files. In the early 1990s, Mr. Rupert worked for Geico Insurance, representing the company at mediations. In 1994, Mr. Rupert was certified by the Florida Supreme Court as a mediator.

In 1996, Mr. Rupert formed his own firm, and has handled thousands of cases since, primarily in personal injury, but also nursing home liability, contract disputes, consumer rights, products liability, real estate and property disputes and divorce cases in circuit and federal court.

In 1998, Mr. Rupert became a member of the Academy of Experts, a mediation and law society in London, England. They specialize in expert witnesses for trial, mediations and international dispute resolution. The chairman is Lord Howe, former British foreign minister. Mr. Rupert also assisted the Law Society of England and Wales in drafting the procedural rules for mediation now used in those places.