In 1972, he enrolled in the Columbia School of Broadcasting, a correspondence course, and after completing the program, began his radio career at WRYT in Boston as a staff announcer and control board operator.
He was also the only music disc jockey on the airstaff to move to the new format, co-hosting WRKO's Morning Magazine program with Norm Nathan for two years.
[citation needed] In February 1973, Stephens was instrumental in one of the most ambitious promotional stunts in Connecticut radio history when he locked himself inside the WCCC AM&FM on-air studios in Hartford and played the Top 40 song "Bitter Bad" by Melanie for 35 consecutive hours to protest the station's reluctance to offer him a full-time job.
Stephens moved back to Osterville in October of that year, and after taking several radio announcer positions on Cape Cod and in Boston, he founded his own TV production company, Ultimate Garage Productions, Inc. Stephens serves on numerous automotive and motorsports television productions as a host, commentator, automotive expert, and pit reporter and has been seen on CBS, NBC, ABC, ESPN, ESPN2, ESPN Classic, Fox, Fox Sports Net, SPEED, The Discovery Channel, Discovery HD Theater, Velocity, The Outdoor Channel, The Family Channel, and HDNet.
He co-hosts the series "RVing in the USA" on Motor Trend TV and has written, produced, and narrated numerous automotive and motorsports home videos in national distribution.
In 2011, he researched, wrote, produced, and narrated the National Hot Rod Association's 60 Greatest Moments video to commemorate the NHRA's 60th anniversary.
In 2014, he traveled to France, Monaco, and the French Riviera to write, produce, edit, and narrate the award-winning documentary "Henri Chemin and the Lost Hemi".
In 2016, Stephens was chosen to provide his automotive expertise as an interview subject in the production of the docu-drama series "The Cars That Made America" on the History Channel.
His hosting duties at the Petersen Automotive Museum were also acquired for the "Tribute to George Follmer" in 2016, honoring the 1970 SCCA Trans Am World Champion with co-driver Parnelli Jones.
Working with his substantial database covering automobiles and light-duty trucks from the 1940s to the present, Stephens provides appraisals for his clients reflecting real world value estimates in the constantly fluctuating marketplace.