People aren’t born great leaders. They learn to become great leaders.
For Brian Chesky, the learning never stops. As the co-founder of Airbnb, he had to transition from an impassioned entrepreneur with a brilliant idea into a CEO responsible for thousands of employees. To make the hard decisions necessary for Airbnb to survive the COVID pandemic, a cataclysm ... Show More
Oct 20
Revisited: The Power of Doing One Thing Exceptionally Well with Gymshark Founder and CEO Ben Francis
Hello from Team Simon! Brand-new episodes of A Bit of Optimism are back next Tuesday, October 27. Before then, we're revisiting one last favorite: the company Simon names whenever someone asks which business actually lives the ideas he writes about. It's Gymshark, and its founder ... Show More
1 h
Oct 13
Revisited: Why Relationships Are the Secret to a Long, Happy Life with Psychotherapist Esther Perel
Hello from Team Simon! We’re taking a few weeks off and will be back with brand-new episodes of A Bit of Optimism on Tuesday, October 27. Until then, we’re revisiting some of our favorite conversations, including this one with a longtime friend of Simon’s: Esther Perel. For most ... Show More
1h 2m
Apr 2023
A Dream, Disruption, and Airbnb’s Greatest Challenges with Brian Chesky
Since Brian Chesky and his then-roommate rented out three air mattresses in their apartment in 2007, he’s been on a wild ride building Airbnb. What are the biggest challenges of building an $80-billon dollar business and disrupting the hospitality industry in the process? How do ... Show More
47m 30s
May 2025
CEO Diaries: Airbnb’s Founder Brian Chesky on Brutal Rejection, Great Leadership, and The Biggest Mistake Founders Make!
From cold emails to global dominance - the Airbnb story began with rejection. In this unmissable episode of CEO Diaries, Airbnb founder and CEO Brian Chesky reveals the brutal truth about rejection, resilience, building world-changing companies, and the one thing more important t ... Show More
13m 30s
May 2023
Airbnb’s Next Phase — with Brian Chesky
Brian Chesky, the co-founder and CEO of Airbnb, joins Scott to discuss a slew of updates, including how the firm is building a community, leveraging AI, and expanding its geographical reach. We also learn about Brian’s experiences with loneliness, and how work has impacted his re ... Show More
1h 5m
May 2022
Airbnb's Brian Chesky: Do things that don’t scale
In honor of our five year anniversary of Masters of Scale, we're revisiting our first episode ever, featuring Airbnb's Brian Chesky.If you want your company to truly scale, you first have to do things that don't scale. Handcraft the core experience. Get your hands dirty. Serve yo ... Show More
30m 26s