Design Of Podcast

Billy Oppenheimer is a pattern-seeker, storyteller, and creative thinker who turns curiosity into clarity. His path, from ski towns and side jobs to working alongside bestselling author Ryan Holiday, is a powerful reminder that following what fascinates you isn’t a distraction; it’s a direction. In this episode of Design Of, Billy shares how his instinct to notice, capture, and connect ideas has shaped his creative journey, and how it continues to evolve through deep research, disciplined writing, and his upcoming book with Penguin Random House, The Work Is the Win. Billy’s creative trajectory began with a bold, curiosity-fueled email to Ryan Holiday, whose own career was launched under the mentorship of Robert Greene (The 48 Laws of Power). That lineage, Greene to Holiday to Oppenheimer, reflects more than just professional mentorship. It reveals a shared creative philosophy: do the work, think deeply, and trust that the process itself holds the reward. Now, through his widely followed newsletter Six at