If Bobby Schlesinger aspires to the ranks of Ian Schrager and André Balazs, he’s not currently emulating their lifestyle. He arrives to our meeting on foot, having stepped not out of a Bentley but a New York City subway train, politely explaining that the choice of a vegan restaurant is due to his sister-in-law’s recent conversion. There’s no Tom Ford suit with a generous flash of clavicle; instead, Schlesinger looks his boyishly handsome 25 in dress pants and a checkered oxford, whose pink polo pony elicits some playful teasing from our Kirsten Dunst-lookalike waitress. “Would I like to date Uma Thurman and be a successful businessman? Sure, who wouldn’t?” Schlesinger says when asked where he sees himself among those majordomos. “But I don’t want to be a celebrity hotelier. I’m not in this business to be a personality.”

Whether intentional or not (and he assures me it isn’t), Schlesinger has emerged as the face of The Obadon Hotel Group, a family-run portfolio of luxury properties in Palm Beach and Miami. Obadon is the hotel arm of Ceebraid-Signal, which was founded in the 1950s when Schlesinger’s grandfather Gilbert began buying multifamily real estate in the New York metropolitan area and which quietly grew to include some 15,000 residential units up and down the East Coast. Today Obadon comprises The Mayfair Hotel & Spa in Coconut Grove, The Brazilian Court Hotel & Beach Club on Palm Beach, The Traymore on Miami Beach (currently under construction) and the most recently opened, The Omphoy Ocean Resort on Palm Beach. Schlesinger says it was his father, Richard, the managing director of the company, who first took the business in the luxury direction, thus giving rise to Obadon. “The first superluxury thing he did was a condominium on Palm Beach Island called Il Lugano.” Less than a dozen units, Il Lugano was the first modern incarnation of its kind on Palm Beach, and enjoyed an unprecedented level of success for the family, providing an incentive to expand in a new direction.

The Brazilian Court had been a landmark of old Palm Beach exclusivity since the 1920s, but by 2002, the property was long in the tooth and up for sale. Richard—together with middle son Adam (Obadon’s COO)—acquired the property, investing $35 million and transforming it into a secluded oasis of elegant Spanish courtyards framed by stucco arches and palm gardens. “If we didn’t go out and pursue people like Daniel Boulud and Frédéric Fekkai, I don’t think our business would have taken off the way that it has,” says Schlesinger, referring to the celebrity chef and stylist who both opened outposts at The Brazilian Court. “And it has been frequently copied,” he continues, his voice mixed with a certain brio. “Not to say that we started the trend, but I would hesitate to name another developer, in their first hotel project, who achieved partnerships with the likes of those two.”

Despite the confidence and obvious pride in Obadon’s accomplishments, Schlesinger admits that joining the family business wasn’t always a given. “My mentality was, I don’t want to go into the family business because I’m just going to be another son studying real estate behind two brothers,” he explains. For some it could have taken on shades of a Balthazar Gettyesque rejection of birthright, but far more simply, and practically, Schlesinger just didn’t see where he fit in. After a stint at Deutsche Bank and some flirtations with a sports-agent career, Schlesinger realized that while his father and brothers (eldest brother Jason is involved with Ceebraid-Signal but not Obadon) had built a solid framework of business models, acquisitions and development, the day-to-day operations of the hotels were not being handled within the fold. He says his thoughts became, “We now have a hotel and there’s no one who knows how to operate these types of things. You’d better start learning this business.”

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