Episode 129: Brian Chesky

5 Questions With Dan Schawbel

My guest today is the co-founder and CEO of Airbnb, Brian Chesky. Brian is the epidemy of rags-to-riches having gone from not afford rent with his co-founder to founding the multibillion-dollar hospitality company Airbnb. Through his leadership, the company is used by more than 500 million customers in 191 countries. Despite being one of the biggest success stories in his entire generation, Brian is down-to-earth and shared some valuable insights from his life during this podcast episode.

The 5 questions I ask in this episode:

1. Both of your parents were social workers. What values did they instill in you that has made you the leader you are today?
2. The hospitality industry was one of the biggest victims of the pandemic. You and Airbnb reacted to Covid by creating online experiences, offering a $250 million support package to hosts, and more. But, can you talk about how you managed the mental and emotional hardship of navigating the crisis while overseeing thousands of employees, and millions of hosts and customers worldwide?
3. Airbnb has come a long way since you co-founded it back in 2008. I recently stayed at an Airbnb in Miami, but if I said that to my parents a decade ago, they would have reacted stating “what’s that?” or “just stay at a hotel it’s safer”. What do you think originally led to the acceptance of Airbnb and how has its growth affected how you live and relate to other people in your life?
4. In my last book, Back to Human, which was published just before Covid, I tell people to “use technology as a bridge to human connection instead of letting it be a barrier that isolates them from others.” In the foreword for Airbnb’s “Travel Report,” you emphasize this by saying that “technology has provided a means of digital connection, but this is more synthetic and less fulfilling than real human connection”. I think only robots would disagree with our perspectives. How have you used technology as a bridge to real human connection with your family, friends, and team?
5. What is your best piece of career advice?

Video interview

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