Thursday, January 27, 2022 Jan 27, 2022
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James Chippendale

James Chippendale of CSI Entertainment Insurance on waiting tables, U2, and his battle against cancer.
By  |
photography by Elizabeth Lavin

James Chippendale has had a knack for developing niche insurance programs since his early days at management agency Gregg-Miller & Associates. In 1994, Chippendale founded CMI, which later became Dallas’ CSI Entertainment Insurance, after recognizing the need for personalized insurance covering concerts and sporting events; the category can include everything from event cancellation and liquor liability to protection for volunteers and teams against bodily injury and litigation costs. When the Rhode Island nightclub fire took the lives of 100 people in 2003, Chippendale’s business quadrupled overnight. Now CSI is one of the country’s largest entertainment-insurance brokers, with 15 employees and a projected income of $12 million this year. The firm provides  coverage for more than 3,500 concerts and special events each year, insuring everything from Lollapalooza and REM to Lance Armstrong’s cycling team and Patti LaBelle. Chippendale’s CSI office is located in Deep Ellum—fitting for the music-loving CEO who’s known to attend most of the events his firm covers.

Age: 39

Title/Company: President and CEO/CSI Entertainment Insurance

Tenure: 15 years

What was your first job? Washing dishes at a Dallas restaurant called Peppers. I worked my way to busing tables and then waiting.

What was your worst job? Working at a place called The Rusty Pelican in Dallas. I would smell so bad when I came home my mom would make me strip my clothes off as soon as I walked in the door.

If you couldn’t say “the people I work with,” what would you say is the best part of your job? Being a part of the experience. The people, the music, the whole experience.

What is overrated in your job? I used to be that guy who thought making money was what mattered. But it’s all about having great people and experiences. Some people are so miserable because they are connected to this thing they created based on material things.

What’s you favorite place in Dallas? [Plano’s] Arbor Hills. Dallas can get so brass and concrete, so to find this little gem with its trails and hills is nice.

What book is on your nightstand? A New Earth by Eckhart Tolle. It’s about living a good, positive life.

What’s your favorite TV show? South Park. It’s my 30 minutes of mindless fun every night where I don’t have to think or analyze—and it’s still intelligent and current.

What’s your most recent major purchase? I tend to spend my money on experiences rather than material things, though I do have a shoe fetish. Mostly my purchases go along with traveling.

What’s your favorite type of music? My favorite artists are New Order, Massive Attack, and U2. I’m all across the board, classical to punk. 

What’s the best advice you’ve received? “Don’t be attached to the outcome.” That helps me focus. If I don’t get a deal, that’s OK. I don’t stake my identity on the outcome.

What has been your greatest challenge? Battling cancer. I had an excellent assistant to run my business for three years while I struggled. I [approached] cancer with a business mind; I analyzed it and learned as much about my enemy as possible so I could fight it.

What is your passion?
My foundation, the LoveHopeStrength Foundation. We produce concerts around the world to raise money for cancer centers, so everyone can have access to the best doctors and research. Our goal is to have a cancer center in every country in the world.

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