In this 2016 conversation, Bonny Simi—Olympian, airline pilot, venture capitalist, and entrepreneur—explains how success is built on curiosity, creativity, and the courage to take risks. While in her role with JetBlue, Simi shared how setting bold intentions, building transferable skills, and leveraging parallel career moves shaped her unconventional career. Her insights aren’t just for entrepreneurs—they serve as a reminder that this mindset can be applied to any area of life. With advice like taking risks with confidence and being open to non-traditional paths, Simi—now the president of operations for Joby Aviation—highlights the power of small steps, resilience, and trusting the journey.