Caldara, who hosts a 3-hour-a-day radio talk show on News Radio 850 KOA, was named by 5280 Magazine as one of the top 10 most influential men in Denver. Westword has awarded Caldara the title of "Denver’s Best Media Manipulator." In 2005, he was presented with the Thomas Roe Award by the State Policy Network.
In addition to his radio talk show, Caldara hosts a current affairs television program, "Independent Thinking" on KBDI Channel 12 in Denver on Fridays.
Caldara studied economics and business at the University of Colorado in Boulder in the mid-1980s, where he pioneered a daily comic strip, B Street, that was eventually syndicated to more than 50 newspapers across the country.
In 1994, Caldara was elected to the Board of Directors of the Regional Transportation District (RTD), the fourth largest governmental entity in Colorado. In 1998, he became chairman of the organization after leading an effort in 1997 to defeat "Guide the Ride", a 66% sales tax increase.
In 2005, Caldara led the campaign to defeat Colorado State Borrowing Act, Referendum D (2005).