James Chippendale may never be able to go to a concert and completely relax. That’s because, as the CEO of an entertainment insurance company, he gets paid to worry.

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A NORMAL PERSON MIGHT JUST SEE A TOUR BUS. James Chippendale pictures it careening through a barricade. What looks like a crowd of music lovers to most conjures images of massive unrest in this man’s mind. Chippendale sees disaster at every turn, and for the people who rely on him, that’s a very good thing.

“I look and think, ‘What can go wrong?’ ” he says. “I’m the Debbie Downer of the party.”

His company, Dallas-based CSI Entertainment Insurance, offers insurance services and risk-management coverage to a specialized niche of musicians, venues, concerts, and festivals -- 3,000 of them a year -- bringing in a total of $8 million annually in revenue.

“The stage could collapse and a person could die. What if a Category Five hurricane were to blow in?” asks Chippendale, 40, who started CSI 15 years ago. “We’re kind of the grim reaper, but that’s our job. We’re there to make the environment safe.”

CSI is the link between insurance carriers, which write the policies, and the entertainment industry, which needs them. The industry’s needs are highly specific and include coverage for workers’ compensation, equipment, cancellation, vehicles, and vendors. There’s also the less-standard coverage for mayhem, conflagration, and explosion to consider. “We had an RV blow up once from a faulty generator, and a car caught on fire in a parking lot,” says the Texas-born CEO. “Another time, high winds blew over some scaffolding and the guys on it had to jump off as it was coming down. The worst was when Limp Bizkit was onstage. Fred Durst, the lead singer, encouraged people to start rioting.”

Chippendale grins. “Some carriers don’t like heavy metal.”

These days, CSI has boosted its client roster with a slew of high-flight performers, including George Strait, Gwen Stefani, Ludacris, Kenny Chesney, and the Dixie Chicks. The company also covers two of the country’s largest annual music festivals: Austin City Limits in Austin, Texas, and Lollapalooza in Chicago. And it provides insurance for TV and movie projects and athletes as well; among those covered are Michael Moore’s film festival and Lance Armstrong’s cycling team.

“You can’t be in this business and not be covered,” says Gary Weinberger, president of Alabama-based Red Mountain Entertainment, which promoted 110 concerts and events last year. “We wouldn’t dream of doing an event without consulting James.”

CHIPPENDALE came to his career in a typical way, taking a job at a general insurance company in Dallas after attending Arizona State University. Within two years, though, the entrepreneur mantra began to sound in his head. The company is getting half of what I’m making, he kept saying to himself. So, he began writing insurance policies for friends who owned local live-music bars and nightclubs, zeroing in on short-term special events, known in the industry as one-offs.

“The more I talked to people, the more I saw that there was no expert in this segment of the market,” he says. So Chippendale became that expert. In just five years, CSI had secured contracts with about 70 percent of the music venues in Dallas and Austin, as well as with 400 other clients nationwide.

At first, his motivation was mercenary, he admits: “I was driven by my material place in the world, how much I could make. I thought I needed to keep up with everyone else.”

But while he was more than keeping up, Chippendale -- whose success was founded entirely on the notion of preparedness -- took an ironic hit that changed his thinking from that point forward. In 2000, he was diagnosed as having a potent form of leukemia and given unfavorable odds of survival.

“I went at my illness as a business and asked myself, What do we have to do?” he says. “I drew up a plan and assembled the best team to beat the disease. I found a mind coach who helped me become mentally prepared. I meditated; took no calls, no meetings; limited my exposure to friends and family.” He spent a year in and out of the hospital, enduring three rounds of chemotherapy, radiation, and ultimately a bone-marrow transplant. After three years away from the office, he had made a full recovery.

When he returned to his desk in 2003, the business had been depleted by about a third. To recoup, he took on a partner and began to share the responsibility that he had previously carried alone. “All of a sudden, there was no panic,” he says. “It wasn’t about how much money to make and how fast to make it but about having a good, fun, solid place to work where everybody can make a nice living. Somehow, with that relaxed attitude, the business has become that much more successful.”

A FORMER FABRIC warehouse in Dallas’s Deep Ellum neighborhood (long the city’s nucleus for music and nightlife) has been transformed into a serene, hip, and decidedly non-insurancy insurance office. The 12 CSI employees who spend their days there among birch plywood tables, poured concrete, and bursts of lime are equally atypical for the industry, having been plucked from former gigs on and around the stage. One staffer managed bands, one was a concert promoter, and another ran one of the city’s largest venues for touring acts. Over the course of the company’s history, there have been musicians, bartenders, and club managers selling insurance for Chippendale, who selects his team with clear purpose. “I can teach them the 50 things they need to know about risk management,” he says. “But you can’t go to school to learn the ins and outs of the entertainment industry, which is a crazy business. These guys can walk in and know the pitfalls.”

Paul Bassman spent 15 years managing multiplatinum rock artists before signing on as CSI’s president in early 2007. “When I decided to leave the music business, this was a strange concept. But it made perfect sense,” he says. “What other insurance broker would know what it’s like backstage or how to negotiate a contract with agents, when all they’ve been insuring are buildings or construction sites?” For clients, this savvy is a winning edge. “When someone responds in the same vernacular,” says Weinberger, “you just know you are speaking to a kindred spirit. We don’t want to have to explain what it is we do for a living.”

The fatal fire at a Rhode Island nightclub in 2003 forced insurance executives to reexamine how they were protecting their entertainment- industry clients. Chippendale remembers that prior to the incident, contracts weren’t terribly exacting or formal. “It was more of a handshake,” he says. “No one checked limits or terms.”

But when area suppliers, sponsors, vendors, and even the local radio station were sued for failing to make sure the pyrotechnics at the Great White show were safe, it became clear that proper coverage was critical. “This kicked us into a different level and focus,” says Chippendale. His business increased fourfold overnight.

In the last year, with his livelihood and his health thriving, Chippendale has found a way to use his success, and his contacts in the music industry, for a greater good. He had an idea to host concerts in locales around the globe that have impoverished hospitals and to have the concert proceeds go to those facilities’ cancer centers. He conceived the Love Hope Strength Foundation with musician and fellow leukemia survivor Mike Peters (of the Alarm) and has raised nearly $1 million from four shows so far -- one in the Empire State Building’s observatory in New York; one at Kala Pattar, above the base camp of Mount Everest in Nepal; a third at Mount Snowden, the highest point in England and Wales; and another at the Union County Music Fest in New Jersey. In October, a historic trek will take place at Machu Picchu in Peru, with a closing concert in Lima that is being billed as the largest concert ever held in Peru.

“When I was ill, I couldn’t walk up two steps without getting out of breath,” says Chippendale. “But along with hundreds of other trekkers, I climbed 19,000 feet up a mountain.” The foundation is anchored on the premise that everyone deserves access to proper care, regardless of where they live or how much cash they have. “I was lucky to have the best treatment because I had connections and health insurance. To me, that is not fair.”

Chippendale is happy to have connected his career with this personal mission. “Music crosses all borders,” he says. “You have to take control of your destiny. You only get one shot.”