Serial Entrepreneur

Photography by Craig Denis

Sean Wolfington was destined to be a pioneer. One of those self-motivated leaders who forges paths for the development of unchartered industries. One of those self-taught types who revolutionizes industries through brilliant insight and an ahead-of-the-game mentality. That is who Sean Wolfington was meant to be, and at just 39 years old, he has become all of that and more. Wolfington’s résumé runs the gamut from CEO of Wolfington Companies, film producer, digital marketing expert, and automotive pioneer, to all-around family man. He is an entrepreneur in every sense of the word, with experience in the realms of technology, finance, real estate, film, auto, and charity.

The great, great grandson of one of the first carriage makers in the automotive industry, Wolfington’s entrepreneurial gene is inherent. His grandfather owned one of the first automotive dealer groups, his father was an automotive retailer, one uncle invented the automotive car lease, and another founded Carey International. An appetite for tackling new ideas is in his blood, as well as in the blood of his many extended family members. Of 86 first cousins on the Wolfington side alone, all but a handful run and operate their own businesses in the fields of transportation, technology, finance, real estate, and energy.

At a young age, Wolfington learned the tools of entrepreneurship from his extended family, and he has been building empires around his ingenious ideas ever since. His first business lesson came when he was seven years old, and his older sister was challenged with selling candy bars to raise money for her school. She was shy while he was industrious—he figured out that by selling the $1 candy bars for an inflated $2, he could gobble up one candy bar for each one sold. This savvy skill was not lost with his youth; at eight years old, Wolfington and his twin brother Ryan launched their first company, “Wolfington Works,” a make-it-happen, do-anything business adept at mowing lawns, babysitting younger children, and taking out the trash.

A native of Pennsylvania, Wolfington has homes in Philadelphia; Avalon, NJ; and Palm Beach, but he lives on Key Biscayne with his wife and four children during the school year. He earned a first-class education at Malvern Preparatory School, and later attended Dickinson College. It was while studying at college that Wolfington began working in the automotive industry. And through years spent working his way up in that industry, Wolfington grew a passion for revolutionizing the business. “I saw what could be and got addicted to perfecting automotive retailing and changing the way the world buys and services their cars over the Internet.” To fulfill this mission, Wolfington co-founded Cyber Car in the late 90s, which grew into one of the largest automotive consulting organizations in the world. Later he partnered with David Boice and his technology company Automark, an automotive kiosk company. Together, Boice and Wolfington grew Automark into the industry’s leading digital marketing company that helped manufacturers and retailers gain the tools and training to sell and service vehicles over the Internet. The companies were doing something never before seen, or even imagined. So when automotive retailing solutions company Reynolds and Reynolds purchased Cyber Car and Automark in 2000 for an enterprise value of $200 million, it was no surprise that Wolfington moved on to blaze new trails.