Jean Case is a prolific executive, investor, philanthropist, and impact investing pioneer. She is the Chairman of the National Geographic Society and CEO of the Case Foundation, which has been recognized for addressing significant social challenges and driving exponential impact. Jean is also the author of her latest book, Be Fearless: 5 Principles for a Life of Breakthroughs and Purpose. Jean is dedicated to social impact and she and her husband Steve Case joined The Giving Pledge and publicly reaffirmed their commitment to give away the majority of their wealth to fund worthy charitable causes. In today’s episode, Jean talks to us about how to take big bets, how to step outside of your comfort zone, and what it really takes to create a big vision and an extraordinary, fearless life. The 5 principles of being fearless (4:10) The importance of “failing in the footsteps of giants” (5:44) Social media’s impact on perceived success (6:15) How to create urgency in your life even without life threatening situations (8:24) Taking the long view in life (9:12) The early stages of growth at AOL from startup to a “10 year overnight sensation” as the first internet company to go public (11:08) How to leverage disenfranchisement to your advantage (15:38) How your brain can trick you even when you know you’re safe (22:00) Some questions we discuss: How did you overcome your fear of risk? (19:44) How to differentiate between what’s real fear and what’s not? (21:11) Are you someone who has mostly done things in your life you’re sure you could be good at? (20:54) How do you start right where you are? (25:21) What is your experience as a woman in tech? (27:57) “The world might count you out, but don’t be the one who counts yourself out. Stay in the game, keep the long view”