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
Sep 15
The Dating Advice Making Us Worse at Love with Relationship Expert Amy Chan
The internet is flooded with advice for dating in the smartphone age: know your type, trust the spark, watch for red flags, protect your peace, never settle. It sounds like self-respect, but relationship expert Amy Chan thinks it’s a big reason dating feels impossible right now. ... Show More
50m 17s
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