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Brian Chesky on Happiness, Success, and the Importance of Relationships

Published: at 04:10 PM

Source: “Brian Chesky on Happiness, Success, and the Importance of Relationships” from the “Jay Shetty Podcast”

Link: https://www.youtube.com/watch?v=g5GaBnavBrY

Date: September 11, 2023

Brian Chesky, the co-founder and CEO of Airbnb, discusses his views on happiness, success, and the importance of relationships in a conversation on the “Jay Shetty Podcast”. Here’s a summary of key points from the discussion:

Key Insights

Loneliness as a Major Issue

Chesky highlights loneliness as a critical problem in America, even more harmful than smoking. He notes that loneliness can lead to mental health issues, with a large percentage of adults and teenagers experiencing it. He believes that it stems from a disconnection from oneself and others.

Shifting Definition of Happiness

Initially, Chesky equates happiness with achieving success and “climbing the mountain,” but later realizes that true happiness comes from working with people he loves on ideas he is passionate about. He emphasizes that his motivation shifted from self-focused achievement to giving to others and focusing on the work itself. He explains that the best part of success is choosing who to work with.

The Journey Inward

Chesky describes the importance of the internal journey, or the journey “inwards to the valley,” as much as the external one of achievement. He says that the process of building a company has taught him a great deal about himself and that a company is like a mirror reflecting the founders.

The Power of Relationships

Chesky values deep, meaningful relationships and describes his co-founders as a “family”. He stresses that the best decision he made was to prioritize friendship over winning arguments. He says that shared values are important in building a strong team. He emphasizes the importance of having people in one’s life who see potential that one may not see in themselves. He believes great relationships improve with age, give energy, and pull out creativity.

The Amplifying Effect of Success

Chesky notes that success can amplify both positive and negative qualities within a person. He explains that success can also lead to isolation and loneliness if not balanced with meaningful connections.

The Importance of Community

Chesky expresses his intention to shift the focus of Airbnb from a travel service to a travel community, aiming to design connections between people and combat loneliness. He believes that a community, unlike a product, can help with the problem of loneliness.

The Role of Design and Creativity

Chesky describes himself as a designer at heart, seeing Airbnb as a canvas to create and connect things. He believes that companies should be more design-driven, incorporating both the head and heart. He emphasizes the need for more creative people in leadership roles.

Living Authentically

Chesky explains that as a leader, he realized he was performing for an audience and that his challenge was to evolve and not be confined by others’ expectations. He emphasizes that it is important to listen to your own voice and that it is okay to be misunderstood, as revolutionary ideas are often initially dismissed. He states that he is still trying to understand what makes him happy, particularly on a personal level.

The Value of Service

Chesky recalls a pivotal moment during the war in Ukraine where he was compelled to ask how he could help, which resulted in providing housing for over 100,000 refugees. He says that helping and giving to others brings him happiness.

The Integration of Personal and Professional Life

Chesky explains that his personal life was put on hold in the early years of Airbnb. He says his clarity around his professional life came earlier than his personal life, where he still is seeking that clarity. He believes that you find what you seek by starting and keep moving. He realized that he designed a company that reflected the world he wanted to live in, but he needed to live in that world.

The Power of Zooming In and Out

Chesky discusses his leadership style of being able to zoom in and out to see the big picture and the smallest details. He explains this practice is important in order to be able to lead and also connect with people at an intimate level.

The Iconography of Self

Chesky reflects on how the company and his personal identities merged and that he became a symbol instead of a person. He says that his personal iconography is based on family, community, and love and that he sees himself as both the curious child and the protector.

The Power of Paradoxes

Chesky explains that the paradoxes and tensions of the world are the things that make life fascinating. He also explains that the connection is what makes it all happen because everything is interdependent.


Chesky’s journey underscores the importance of self-awareness, genuine connection, and the pursuit of a life driven by purpose and love, rather than external validation. He believes in the potential of community and the power of human connection to address significant issues such as loneliness.


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