After being virtual friends with Josh for some time, we finally had a chance to meet him in person last October. Friendly, upbeat, and instantly likable, Josh has a contagious laugh and an optimistic attitude toward life. Since saying goodbye to his role as principal designer at Twitter, Josh has ventured out on his own, but this isn’t the first professional—or personal—risk that Josh has taken over the course of his winding path. After a music-filled childhood, Josh spent his teenage years wanting to be an art teacher; instead, he had a brief stint teaching kids to use computers, which sparked his interest in the web, and the rest is history. We talked with Josh about his work in the startup world, his decision to leave Twitter, the responsibility he feels to do meaningful work, and what he’s up to next. —Tina