Karen Dalessandro on Reinvention, Radio Gypsy Life and Becoming a Hall of Fame Broadcaster

In this episode of Off Deadline, host Melissa DiGianfilippo sits down with Karen Dalessandro, a multi-award-winning broadcaster whose career spans more than four decades across Detroit, Chicago, Milwaukee and Phoenix. Karen shares how a high school radio booth sparked her passion, the advice that pushed her into country radio, and the “radio gypsy” lifestyle that shaped her early years.

She opens up about sitting in all 60,000 seats at Miller Park to raise money for child abuse prevention, launching mammogram parties to help women get screened, meeting Taylor Swift before her superstar era, and becoming only the third woman ever inducted into the Country Radio Hall of Fame. Karen also reflects on 40 years of marriage, navigating loss, leaning on fitness, and reinventing herself again and again through a constantly changing industry.

Karen can now be heard every afternoon on @1007kslx, where her signature energy continues to connect with listeners across Arizona.

Discussion highlights:

• How a high school radio class sparked her career
• The mentor who pushed her into country radio
• From Detroit to Chicago to Milwaukee to Phoenix
• Radiothons and sitting in 60,000 stadium seats for charity
• Creating mammogram parties and their lasting impact
• Meeting Taylor Swift as a 15 year old “baby artist”
• Becoming the third woman in the Country Radio Hall of Fame
• Surviving the record industry lifestyle in her marriage
• Grief, growth and finding a new dog after loss
• Fitness, certification and staying sharp as a broadcaster
• Why improv changed her confidence and her career
• Reinventing herself for TV and multimedia storytelling

Karen’s story reflects passion, longevity, risk taking and the power of reinvention in media.

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