An apprentice grows up

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.

Rancic spoke to the Business Observer before the Tidewell event about his early business career. “For me it was survival,” says Rancic. “You have to know going in you are going to go a while without getting paid and you will have to sacrifice. You have to be OK with that.”

Rancic, in addition to several TV shows, including the reality show “Giuliana and Bill,” with his wife, Giuliana Rancic, has several business interests. The couple owns two restaurants in Chicago, and they sell a line of wines in shatterproof cups. Rancic, also a real estate developer, talked about several other lessons:

Stay nimble: Rancic says one key to his success is the ability to shift strategies on new information. “You have to be agile and have to adapt a lot with what's happening,” Rancic says. “You have to go where the fish are.”

Team up: “The most successful business people I know are the ones who don't do it alone,” says Rancic. “They are like an orchestra conductor who can't play all the instruments but can make beautiful music.”

Maintain the passion: Rancic says he keeps his projects list full because that motivates him. “Some people like structure,” Rancic says. “But I like it when I have a lot of different things going on.”