Richard Kessler was just 24 when he stumbled into the lodging industry. It was 1970, and he had begun helping a man named Cecil Day develop apartment complexes in Georgia. That summer, Day vacationed in California, and his family’s stay in a Motel 6 forever changed his fortunes and those of his young colleague. Kessler says Day returned home with the inspiration to start a similar chain of budget motels on the East Coast. Within weeks, Days Inn was born.
In 1972, eager to expand across Florida, the two men pooled their money. “He put in $700. I put in $300, and I borrowed millions. We built the company out of it,” Kessler recalls. By age 29, he was president and CEO of Days Inn, which is now part of Wyndham Hotel Group. Kessler built nearly 40,000 motel rooms while generating giant returns that increased by 35 percent each year for nearly a decade. “We built a heck of a reputation during that period,” he says.
Armed with his savvy business acumen and a bulging bank balance, Kessler left Days Inn when it was sold in 1984. He focused on land development and banking interests until his heart led him back to lodging. With the inception of the Kessler Collection in 1995, his sights were set on high-end boutique hotels, each with its own “personality.”
The collection that began with the Castle Hotel along International Drive in Orlando has expanded to a total of 10 distinctive properties—from a 15-room ranch surrounded by 23,000 acres of unspoiled Colorado wilderness to a luxury hotel in downtown Orlando boasting more than 150 works of art. With three new projects in the pipeline and West Coast development aspirations, Kessler is focused on expanding his carefully curated collection.
Over the years, Kessler has seen a number of hoteliers, big and small, move into the boutique niche. He politely pooh-poohs the carbon-copy designs of the large chains. He calls them “contemporary-style hotels,” not boutiques. It’s the individuality of Kessler’s hotels that he thinks sets them apart from other properties of the same genre. “Each of our hotels has a different personality,” he explains. “Each is a different design architecturally. Second of all, we put a tremendous amount of original art in our rooms and in the public spaces, far more than any other hotel I can think of.”