Steve Chessare's career is a story of true passion for an industry that began when he was just seven years old listening day and night on his transistor radio, and his love has only grown stronger since. Even at times when it seemed as though his professional life could have gone in more traditional, stable directions, radio always proved to be his true path. Whether it was the neighbor down the street who helped him get his first professional radio job at WBEC in Pittsfield, Massachusetts, or the persistent recruiter who finally revealed that the seemingly uninteresting HR job she was pitching to Steve was, in fact, for the parent company of NBC radio in New York City, or most important, when his late father told him that he ought follow his dream to work in radio, even when it didn't seem to be the most lucrative path - radio is simply in Steve's blood. There have been many highlights and twists and turns, including the most recent realized dream of Steve taking ownership of a cluster stations on Cape Cod: WFRQ-FM/Harwich Port, WHYA-FM/Mashpee, WPXC-FM/Hyannis, WKFY-FM/East Harwich, which he hopes to be just the start of a growing company, Coxswain Communications.

In our conversation, we cover a lot of ground, including the mentorship of his late father Mr. Joseph Chessare, who served as the VP of Beloit Corporation, the trust factor of local radio that distinguished itself as local TV's trustworthiness has eroded, how the large players in the industry have begun to realize the importance of locally-focused content, which was only further highlighted by the pandemic, the art of great programming in radio, Steve earning a reputation as a fixer for troubled companies in the industry, the opportunity for radio to be personal and intimate with the audience, his start in radio at Fairfield University, the early days at WBEC in Pittsfield and WPYX 106.6 in Albany, working for a defense contractor while moonlighting on the airwaves, a remarkable run in HR roles that brought him into NYC and back into radio, being recruited into a position prepping for the firing of Howard Stern, a leap into sales, massive, record-breaking success at CBS Radio in NYC, the turnaround of Westwood One audio network, and finally closing on ownership of radio stations on the Cape and his hope to own some stations closer to home in the Berkshires. 

I hope you'll enjoy my conversation with Steve Chessare.