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.

Payal Kadakia's 2022 conversation feels as relevant as ever, highlighting the enduring importance of authenticity in strong leadership. In this episode, the founder of ClassPass and the Sa Dance Company shares how integrating her full identity—as both a dancer and a business leader—was crucial to her success. Kadakia discusses the importance of listening to your calling, making values-driven decisions, and resisting the pressure to conform to conventional paths. Her insights on aligning passion with purpose, overcoming failure, and redefining success make this episode a must-listen for anyone aiming to build something meaningful while staying true to themselves.

The episode first aired on February 16, 2022

Justin Kan is an entrepreneur and investor best known as the co-founder of Twitch. In this conversation from 2021, Kan shares candid insights on the highs and lows of entrepreneurship, emphasizing the importance of resilience, self-awareness, and personal well-being. Reflecting on his journey—from founding Twitch to reassessing his motivations—he discusses the challenges of chasing external success and the shift toward finding fulfillment in daily habits, mindfulness, and meaningful work. His perspective highlights how true satisfaction comes not just from achievements, but from aligning one’s work with personal values and well-being.

The episode first aired on October 6, 2021.