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Jay Shetty Podcast

Airbnb Founder: The Number 1 Thing People Get Wrong About Happiness and Success | Brian Chesky

Today, Airbnb co-founder and CEO, Brian Chesky joins us on the podcast. In this episode, Brian is honest, vulnerable, insightful, and most of all human.

Brian CheskyguestJay Shettyhost

Sep 11, 20231h 40mWatch on YouTube

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CHAPTERS

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Chapter summaries

Cold open: Loneliness as the hidden cost of success
Brian Chesky opens with a stark message he heard: loneliness can be deadly. He frames success as something that can amplify isolation and raise an identity question—being known as a person versus being known as the company.
- •A mentor tells Brian that loneliness is the “number one killer” in America
- •Brian says success amplified his loneliness and no one warned him about it
- •He describes realizing he may have had what he needed before the success journey
- •He questions whether he’s remembered as himself or “the Airbnb guy”
Setting the stage: Jay welcomes Brian and frames success beyond achievement
Jay Shetty introduces Brian Chesky and his work, emphasizing the tension between scaling success and keeping meaning. The conversation is positioned as an exploration of happiness, connection, and what success costs internally.
- •Jay introduces Brian as Airbnb’s co-founder and CEO
- •Jay highlights building, scaling, and continuing to make something ‘matter’
- •The episode is framed around happiness, healing, and connection
- •Brian expresses excitement to dive into a deeper conversation
What makes Brian happy now vs. 15 years ago: from status to craft, people, and giving
Brian contrasts his earlier belief that climbing the “success mountain” would bring happiness with his current motivation. He describes happiness now as creating, working with people he loves, and shifting from external validation to intrinsic meaning and generosity.
- •Brian once chased success, status, and the feeling of ‘becoming something’
- •He now sees Airbnb as a creative canvas rooted in design and connection
- •He says success allows you to choose who you work with and be around people you love
- •His motivation shifted from proving himself to giving outward and doing the work for its own sake
Starting a company as a mirror: how entrepreneurship reveals your inner patterns
Brian describes building a company as an intense internal journey with extreme highs and lows. He argues success magnifies personal tendencies, and the organization becomes a reflection of a founder’s strengths, fears, and blind spots.
- •He compares starting a company to “jumping off a cliff” and building the plane midair
- •Each new level of growth forces discomfort and self-learning
- •Success can amplify paranoia, narcissism, indecision, conflict avoidance, and more
- •A company reflects a founder’s mind through culture and countless accumulated decisions
Founding Airbnb with friends: protecting the relationship above any argument
Brian explains why founding with friends can work if the friendship is treated as sacred. He emphasizes shared values, complementary skills, and a decision that no single win matters more than the long-term relationship.
- •He compares co-founding to a band that grows from 3 people to thousands
- •The founders agreed no decision would supersede their friendship
- •He highlights the importance of shared values to avoid irreconcilable conflict
- •Complementary skills matter; the “worst case” is same skills with different values
- •He worked to keep co-founders included and publicly recognized as a unit
Believing people are good and mostly the same: travel as empathy and perspective
Brian argues Airbnb reinforced a worldview that people are fundamentally good and “ninety-nine percent the same.” He critiques how digital argument reduces empathy and says real experiences with others are what change minds.
- •Brian says Airbnb data reinforced that people are basically good
- •He argues society over-focuses on the small percentage that makes us different
- •He says “it’s hard to hate someone up close” and experience shifts opinions
- •He criticizes online comment battles as ineffective for changing minds
- •Jay agrees from meeting many people on tour that people are largely similar and good
Loneliness and belonging: from outsider childhood to CEO isolation
Brian traces loneliness back to not fitting in as a kid and describes belonging as a deep human need. He contrasts Airbnb’s early communal “family” culture with the solitude he felt as CEO, especially during the pandemic.
- •Brian describes growing up feeling like an outsider despite mixed interests
- •He says the desire to belong is deeply human and historically tied to survival
- •Airbnb’s early days felt like a tight family living and working communally
- •As he became CEO, he felt lonelier “the higher you get to the peak”
- •During the pandemic he lived alone while working extremely long hours on Zoom
Mentors and reconnection: Obama, friendship renewal, and the role of shared experiences
Brian describes realizing he hadn’t maintained friendships and how a mentor helped him name the loneliness. He recommitted to relationships by creating shared experiences, not just messages, and describes changes he made to rebuild connection in his life.
- •Brian says Barack Obama told him he seemed lonely and should renew friendships
- •Obama described a small set of long-term friends who kept him grounded
- •Brian realized many friendships would require “catching up” due to neglect
- •He recommitted to trips and shared experiences, not only texting or calls
- •He spent more time with family, rekindled old friendships, and got a dog named Sophie Supernova
Loneliness as a societal crisis: Vivek Murthy’s warning and Airbnb’s ‘connection’ mission
Brian recounts learning from Dr. Vivek Murthy that chronic loneliness has severe health implications and is widespread. He reframes Airbnb’s next chapter as designing human connection—moving from a travel service toward a community rooted in trust.
- •Brian says Vivek Murthy called loneliness the “number one killer” in America
- •He repeats the claim that chronic loneliness can be worse than smoking a pack a day and shorten life
- •He shares statistics Murthy cited about loneliness affecting Americans and teenagers
- •He links loneliness to broader disconnection—from others and even from oneself
- •He describes a professional mission: designing connections and growing Airbnb into a travel community built on trust
Solitude vs. loneliness, creativity, and learning through diverse experiences
Jay introduces the distinction between loneliness and solitude, and the conversation shifts to inner work and creativity. Brian and Jay connect creativity to curiosity, interdisciplinary experience, and being willing to explore uncomfortable inner spaces.
- •Jay distinguishes loneliness from solitude and describes learning to be alone as a monk
- •Brian quotes Joseph Campbell about the feared cave holding the treasure
- •Jay shares a story about Steve Jobs encouraging an ashram stay to find direction
- •Brian describes his varied background and how dots connect only in hindsight
- •He emphasizes curiosity over status and says more experiences expand creativity
Identity, people-pleasing, and being okay with misunderstanding
Brian explores the pressure of public perception and how success can turn life into performance. He discusses worrying what others think, the value of being misunderstood, and the challenge of evolving when a brand and audience expect consistency.
- •Brian names a recurring thought: “I wonder what they’ll think”
- •He cites Robert Waldinger’s point about regretting a life spent worrying about others’ opinions
- •He says it’s okay to be misunderstood, especially when doing meaningful new work
- •He warns success increases pressure to perform for an audience and appease stakeholders
- •Jay highlights Brian’s idea that it may not matter what people think ‘today’
Clarity, crisis, and rebuilding Airbnb: fearing bureaucracy and learning a new operating model
Brian explains what keeps him up at night: becoming the kind of slow, soulless corporation Airbnb was meant to disrupt. He describes how the COVID crisis forced radical clarity, rebuilding, and a leadership approach inspired by how he learned Steve Jobs ran a company.
- •He fears Airbnb becoming bureaucratic, complacent, and ‘unrecognizable’
- •He describes the shock of losing a massive portion of business early in COVID
- •The crisis forced prioritization—like saving only a portion of your possessions from a fire
- •He recounts learning from Jony Ive and Hiroki Asai about Steve Jobs’ leadership style
- •He describes an “inside-out” model: integrated, lean, idea-oriented, blending humanities and technology
Designing a personal life: icon vs. human, family as a core value, and living inside the world you build
Brian reflects on how becoming synonymous with a company can blur personal identity. He visualizes himself as both child and protector, describes a longing for expanded “family,” and ties his purpose back to connection, interdependence, and living in the world he designs.
- •Brian says he sometimes designs a world for others but forgets to live inside it himself
- •He describes losing himself by becoming a symbol and merging with the company identity
- •He imagines personal “iconography” as childlike curiosity, wonder, and love
- •He shares an image of a large, beautifully designed dinner table with many people
- •They discuss interdependence, curiosity, and service as connecting forces across life
Final Five: favorite advice, purpose, legacy, and a world built on empathy
Jay closes with the show’s rapid-fire Final Five questions. Brian shares concise principles about love, avoiding status, purpose through bringing people together, and empathy through walking in others’ shoes.
- •Best advice: aim for deep love from a smaller group and do things that don’t scale
- •Worst advice: anything centered on chasing status
- •He defines his purpose as helping bring the world together, even in a small way
- •He hopes to be remembered with “We miss him”
- •His proposed ‘law’: everyone should have a passport and be forced to live in someone else’s shoes

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