Joe Gebbia turned a crazy idea—inviting strangers into your home—into one of the world’s most innovative companies. Joe is the co-founder of Airbnb and chairman of Airbnb.org, his nonprofit brainchild that provides housing to people in crisis. He’s been named to Fortune’s “40 Under 40” and Fast Company’s “Most Creative People.” A lifelong basketball fan, Joe is also a member of the San Antonio Spurs investor group. On this episode, we talk about the incredible story behind Airbnb, turning setbacks into opportunities and doubling down on your dreams.

Jess Sims is a top Peloton instructor and the newest member of ESPN’s College Game Day. Widely known for her work as a fitness instructor, Jess left a career in education to pursue her passion. After teaching at studios in New York City, she became a global sensation when she joined Peloton in 2018 as a Tread instructor, teaching classes to over 7 million subscribers worldwide. On this episode, we talk about changing careers, going for opportunities, and stepping into new situations with confidence.