When James Chippendale stepped onto the field at Grant Park in Chicago last Thursday, he was cool and collected. It was the day before Lollapalooza, the 20-year running, three-day music festival that during its inception helped launch the careers of acts like Red Hot Chili Peppers, Pearl Jam and The Smashing Pumpkins. Dressed in a white t-shirt and jeans and wearing a black baseball cap and dark sunglasses, a passerby would likely mistake him for a touring band member, and not the insurance agent in charge of the entire festival.
“I’ve always been in hospitality ever since I was 15 years old, whether that be bartending in a restaurant or assistant managing a bar—even all the way down to doing dishes in the kitchen,” Chippendale says. “When I [finished college], I went to work for my father’s insurance brokerage firm. I’m actually third generation insurance, so I thought I’d give it a shot.”
His father’s firm specialized in transportation insurance, but when Chippendale started working at the Dallas office, he found it really just didn’t interest him. Without leaving his new job, he instead decided to take what he was interested in—the entertainment industry—and spin it into something that could work.
“I had a few friends in some nightclubs and bars, and I started writing their insurance and I liked it,” Chippendale says. “I went out and developed an entire marketing program to get to more bars and restaurants and nightclubs, and that’s how I really started, [by] focusing on that market segment.”

Diane Rusignola (diane.rusignola@iiaba.net) is IA managing editor.