Bracken Darrell has spent his career helping iconic brands rediscover what makes them matter. In this conversation with Ryan, Bracken reflects on the mindset that guided his work leading transformations at companies like Logitech, Old Spice, Braun, and now VF Corp, home to brands including Vans and The North Face. He shares why curiosity has been one of the greatest drivers of growth in his life, why speed matters more than perfection, and how the best leaders learn to stay optimistic without losing their edge. Ryan and Bracken also explore imposter syndrome, creativity inside large organizations, and the challenge of protecting new ideas from the “gravity” that naturally pulls big companies backward. Along the way, Bracken opens up about becoming more comfortable in his own skin over time and why the strongest brands succeed by helping people feel more like themselves.