Call it good luck or a fluke—fate has a funny way of working. For Jeff Madalena and Jason Gnewikow, serendipity struck at Nowhere Bar, Manhattan’s East Village hang where they met in the early aughts. At the time, both were New York transplants starting small businesses. Jeff, cofounder of rocker-chic clothing brand Oak, had just opened shop in the Williamsburg neighborhood of Brooklyn. Jason, a former musician and graphic designer, was launching a creative agency called Athletics just a few blocks away. The two started dating and soon realized they shared a penchant for ambitious undertakings. "We’re serial project people," Jason confesses. Since then, the couple have grown their individual ventures while starting others together—including a gut renovation of their weekend retreat in the Catskills. It was only a matter of time before they tackled their home base in Brooklyn.