Known for the idiosyncratic websites he created for Beyoncé and fashion labels like the Row, the design wunderkind Matthew Daniel Siskin (above) works within a vast online community. But with his first solo music project, which he’s releasing under the name Gambles, Siskin is seeking a more personal connection with his audience. Trust (out August 27) is folky and intensely personal, a compilation of stripped-down ballads in the vein of Leonard Cohen. For Siskin, the songs express the sort of fierce intimacy usually encountered only in real life. “I like getting as close to the breaking point as possible,” he says.