“So many assistant coaches underneath Tom Landry became head coaches in their own right,” noted Mason, who similarly aimed to influence the next generation of broadcasting leadership. “A lot of people went on to run or lead companies.”
Currently venture partner and strategic adviser at SeventySix Capital, Mason climbed the corporate ladder to the C-suite after humble disc jockey beginnings.
“I grew up in Louisville,” Mason remembered, citing Cawood Ledford, the voice of University of Kentucky sports for decades. “All I wanted to do was be on the radio. He was a great role model to study. I read every word of his book three times.”
Mason’s background reads like a modern-day Horatio Alger Jr. novel.
“I had no intention of ever being an executive,” he reflected. “When I became an on-air announcer, somebody once told me I’ll never get off the all-night show.” That revelation led Mason to soon realizing, “I’d like to be the boss of the disc jockeys.”
Named a GM at 27
Atlanta’s WZGC-FM in 1977 kickstarted Mason’s radio programming trajectory. Two years later, Mason became program director of WPGC-FM Washington, then served as national program director for First Media, the station’s parent company. In 1979, the 27-year-old Mason became one of the youngest general managers in the country at KTSA and KTFM of San Antonio, Texas. He returned to First Media, which was sold in 1988 to Cook Inlet Radio Partners, marking the first time Mason held the president title.
Group W acquired Cook in 1993, then two years later merged with CBS Radio which two years later merged with Infinity Broadcasting.
“I worked with Mel Karmazin until about 2002,” said Mason, who took a five-year break from running the company, albeit remaining a consultant. “Les Moonves in late 2006 asked me to come back as president and CEO of CBS Radio,” Mason said. He oversaw 117 stations across 26 markets, establishing the 24-hour CBS Sports Radio Network and resurrecting the classic hits radio station WCBS-FM New York.
In 2015, Mason “retired” from CBS at 64, leaving to call women’s basketball games for the CBS Sports Network and thoroughbred racing for the Horse Racing Radio Network.
“You don’t retire,” Mason explained matter-of-factly. “Who knows what’s next?”
Indeed, this was no typical early retirement. Whereas most executives would spend more time on golf courses than in front of a camera, on a mic or in a boardroom, Mason’s post-CBS entrepreneurial itch led him to buy several radio stations, consulting with iHeart Radio and VSiN.
“I was going to do on-air talent for horse racing,” Mason said of the latter. After a dinner with VSiN CEO Brian Musburger, a sports agent and nephew of company founder (and legendary sportscaster) Brent Musburger, “it was pretty obvious they really needed me to advise in an executive role.”
A few months later, Mason went from just being an announcer to owning part of VSiN, which was sold to DraftKings four years after its launch in 2017.
Under his CBS watch, executives “flourished,” whether they stayed with the station group or went elsewhere (i.e., the Landry “coaching tree”). Weezie Kramer, who retired in 2020 as chief operating officer of Entercom after nearly 20 years, and Ezra Kucharz, DraftKings’ chief business officer, were among his successful colleagues.
True Radio Lover
Mason recruited Scott Herman as general manager of New York’s all-news WINS after being news director at Group W’s TV station KYW Philadelphia.
Himself retired after 39 years at CBS, Herman last year followed Mason as chair of the Broadcasters Foundation of America. Herman praised his mentor’s ability of securing multiyear financial gifts for the organization. “I don’t think I ever worked with anyone in my career who has loved the medium of radio more than Dan,” Herman said.
Chris Oliviero, currently Audacy’s senior vice president/New York market manager, spent eight years reporting directly to Mason at CBS with his office right next to Mason’s. He said he learned two important things from his former boss. The first was that stations need to create “community and companionship” for listeners. The other is “integrity.” ■
Larry Jaffee was a Multichannel News senior editor and Washington bureau chief in the late 1980s and then managing editor of rival CableVision magazIne. Focusing on other aspects of the media business, Larry was the editor-in-chief of Mediacentral.com, Medialine magazine and Promo magazine. A widely published freelance writer and adjunct college professor, Larry is the author of the new book, Record Store Day: The Most Improbable Comeback of the 21st Century. Larry lives in Washington Heights, Manhattan.
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