The first broadcast was broadcast on November 3, 2002 from 7:00 PM to 11:00 PM in Sarasota, Florida. Free Talk Live became a weeknight show from 7:00 PM to 10:00 PM. After the radio station changed format in June 2003, the show was available only on Internet radio until it was picked up by WTMY, an AM radio station in Sarasota. The show began syndication program in September 2004. Free Talk Live currently airs seven nights per week from 7:00 PM to 10:00 PM Eastern time on over 120 radio and five television affiliates carrying audio simulcasts. In addition to over-the-air radio/TV, the show broadcasts on several internet radio affiliates and XM Satellite Radio channels 166 and 165, on weekdays and weekends respectively.

A major sponsor of Free Talk Live and a Common topic of discussion is the Free State Project, an organization committed to recruiting 20,000 like minded people to move to the state of New Hampshire in search of liberty. Once there, the participants pledge to exert the fullest practical effort toward the creation of a society in which the maximum role of government is the protection of life, liberty, and property. Freeman and Edge moved to New Hampshire as part of the Free State Project in September 2006.

Ian Freeman changed his last name on-air from “Bernard” to “Freeman”. On the September 17, 2008 airing of the New Hampshire-based talk radio show Against The Grain with Gardner Goldsmith, Ian, who was a guest on the show, asked Gardner to refer to him as “Ian Freeman”, not “Ian Bernard”.

The hosts assert that they try to apply the ideals of freedom to their show. The hosts have stated they oppose FCC regulations but still seek to avoid FCC-prohibited speech on their broadcast as it may negatively impact the radio stations that air the show and affront some listeners or trigger the imposition of fines by the FCC against those broadcasters.) The hosts, claiming to adhere to their principles of respecting contract and voluntary agreement, state that adherence to the FCC rules come not at the demands of government agencies but the requests of/or demands by their syndicates. As of March 2009, Free Talk Live has implemented the use of a dump box.

On June 13, 2011, Ian and Mark announced on air that Free Talk Live would be adding a live Sunday show to replace its rotating internet only show, with plans to syndicate the show to radio stations. The show debuted on the internet on June 19 and has since been syndicated on radio.

As of November 12, 2016, listeners contribute a total of $3,179 per month to the show via the AMP program.

Free Talk Live won the Podcast Awards’ Best Cultural/Political Podcast Award in 2005 and won the Best Political Podcast Award in 2006, 2007, 2008 and 2010. The program has been featured in Talkers Magazine's 100 most important radio talk show hosts in America.