- December 13, 2025
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Long before Bill Rancic became a reality TV personality after he won the debut season of “The Apprentice” with Donald Trump, he was a young struggling entrepreneur.
His first success goes back to a quirky marketing ploy when he ran a Chicago-based monthly cigar-by-mail club, Cigars Around the World, in the mid-1990s. Short of money for advertising, he sent a box of cigars with a letter to a radio show producer. On top of the box was a pair of dime store glasses with a note that said, “please take a closer look at my idea.”
The move worked. Rancic, who was in Sarasota recently, where he was the keynote speaker at the Tidewell Hospice Compassion in Caring Luncheon, got a chance to plug his business for 30 minutes on the radio.