Brian Chesky for 1mpacto Magazine

Chesky discussed his early experience attending design school and creating his own “magical” world to “escape numerous challenges of childhood”
In his early days prior to Airbnb, Chesky discussed how he was immersed in the world of design, which led to him attending design school. There, he described how he designed his own “magical” world that was better than the one he was in and to which he could escape, while detailing the challenges he faced in the real world relating back to his childhood, from being “very sensitive and idealistic” to not fitting in at school due to being “hyperactive and impulsive” and considering getting a diagnosis for ADHD [Attention deficit hyperactivity disorder]. This ultimately spurred him on to found Airbnb and to create a sense of “belonging”.

Chesky explained how he had become “addicted to work” and described the “loneliness” of being a CEO while scaling Airbnb
The Airbnb CEO spoke in profound detail about the “loneliness” in his role and his desire to value things differently and prioritise relationships higher, despite calling it the “joy of a lifetime” to grow the company. In a candid discussion, he laid out how difficult it had been to adapt his role as Airbnb scaled to a corporation size, including having boundaries with colleagues but still maintaining the empathy and need to have different opinions around him to make decisions.

In particular, he wished that he made more time for his family [particularly his sister] and also explained how he had developed a close friendship with former US president Barack Obama, who had helped to change his perspective on his values and priorities in life.

Chesky’s “biggest regret” in life so far
Even after scaling Airbnb to the place it is now, at 42 years old, Chesky said he regretted not spending more time with the people he loved and not being able to create his own family yet. Referring back to his “addiction” to work, the CEO detailed how he did not necessarily have regrets about his career as he had already lived “multiple lifetimes” in his job and the things we regret in life are the things “we didn’t do”.

Pondering what he would do if he had ten years left to live, Chesky said that he would want to have more amazing life experiences to share with other people, given that “80 per cent of trips on Airbnb are with other people”.

Being “inspired” by Walt Disney and Steve Jobs
Chesky cites Walt Disney [the founder of Disney] and Steve Jobs [the founder of Apple] as his biggest inspirations in life after having built companies “that lived beyond them”. Like himself, he said that the two late founders were also “creative people leading tech companies” and had a desire to “design something better” – something that is becoming more difficult to find nowadays because “creativity is becoming compressed in corporations”.