A Soaring Passion

Becoming a pilot has fulfilled a childhood dream for InSight Marketing founder Rocco Cipriano.

When he was young, Rocco Cipriano had fantasies that  one day he would soar into the clouds. What  the owner of Harrison-based InSight Marketing didn’t predict is that he’d be doing it in conjunction with the US Air Force. “Becoming a pilot had been a childhood dream of mine,” says Cipriano. Somewhat poetically, that dream came true over a decade ago in classic entrepreneurial style: “I was in negotiations for our marketing services with a business that provided flight training at Westchester County Airport,” Cipriano remembers. “When the client balked at our [price] estimate, I offered to provide marketing services in exchange for flight lessons.”

Since 2001, Cipriano — who boasts more than 30 years of marketing experience — has been founder, owner, and president of InSight, a consulting company that provides direct and online marketing, advertising, public relations, and branding services. Though running the firm keeps him busy, he definitely makes time to get vertical. “One of the benefits of owning my own business is a flexible schedule,” he explains.

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Part of the time, Cipriano takes to the sky as a pilot for the Air Force’s Civil Air Patrol (CAP). “I [wanted] to combine my love for flying with community service and decided to join,” says Cipriano, who’d attended a CAP open house back in 2006. The squadron Cipriano signed up for provides search-and-rescue and disaster relief to the southeastern section of New York, including Westchester County. In nearly 11 years with CAP, Cipriano has been faced with some challenging search missions, including a Danbury plane crash that claimed two lives in November 2015. “I was tasked with two crew members to search for the aircraft,” he says.

Cipriano also volunteers his time as a pilot for two nonprofits: Patient AirLift Services, which flies patients for treatment who can’t fly commercially, and Animal Rescue Flights, which brings animals scheduled to be euthanized to new homes and shelters where they can be adopted. 

Between running InSight, going on missions for CAP, and volunteering with two nonprofits, one wonders how Cipriano spends his leisure time. Well, flying plays a role there, too. He frequently flies for pleasure and has taken friends on day trips down the Hudson River to view the Manhattan skyline from the air. For Cipriano, there’s only one way to go to escape the stresses and pressures of his daily life: up. “There is nothing quite like flying a small plane,” he says. “For me, it offers a tremendous sense of freedom and tranquility.” 

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