Airbnb CEO “IT WAS SO DARK WE NEARLY DIED!”. I Was Lonely, Deeply Sad & Wanted To Be Loved! [INSPIRING!] Brian Chesky

Summary Notes


In a profound conversation, Airbnb CEO Brian Chesky reflects on the company's tumultuous journey during the pandemic, which saw an 80% loss in business, leading to a significant layoff and a subsequent successful IPO. Chesky shares his leadership philosophy, emphasizing the importance of making principled decisions, preserving company culture, and acting with love and empathy, even in crisis. He opens up about his personal growth, the loneliness that accompanied his professional success, and his commitment to rekindling connections with loved ones. Chesky envisions Airbnb evolving beyond a platform for renting spaces to becoming a global community that fosters human connection, combating the pervasive loneliness in society. He aspires for Airbnb to be remembered not just for its services, but for its role in highlighting the shared humanity that binds us all.

Summary Notes

Airbnb's Rapid Decline During the Pandemic

  • Airbnb experienced a catastrophic loss of 80% of its business within eight weeks due to the pandemic.
  • There were concerns about the company's survival and future existence.
  • CEO Brian Chesky faced the challenge of addressing these concerns and making difficult decisions.

"You lose 80% of your business in eight weeks. And I knew there were questions. Is this the end of Airbnb? Will Airbnb exist?"

The quote highlights the sudden and severe impact of the COVID-19 pandemic on Airbnb, raising existential questions about the company.

The Origins and Growth of Airbnb

  • Airbnb started as a way for the founders to pay rent and was not initially envisioned as a major company.
  • The platform unexpectedly grew to accommodate millions of users.
  • Chesky emphasizes focusing on the immediate next step rather than the ultimate goal.
  • He notes that many groundbreaking ideas are initially perceived as crazy.
  • Chesky believes people often misjudge their short-term and long-term capabilities.

"We did not think Airben breakfast would be a company where 4 million people a night would use."

This quote illustrates the humble beginnings of Airbnb and its unexpected growth to a platform used by millions.

The Importance of Step-by-Step Progress and Long-Term Vision

  • Chesky advises focusing on the first step rather than the mountaintop.
  • He suggests that people tend to overestimate their one-year potential and underestimate their ten-year potential.
  • The concept of ten years being a significant amount of time for achieving goals is emphasized.

"People tend to overestimate what they can do in a year and underestimate what they can do in ten years."

The quote encapsulates the idea that long-term progress can be substantial when compared to short-term expectations.

Brian Chesky's Early Life and Interest in Art and Design

  • Chesky had a passion for art from a young age, which defined him.
  • He excelled in drawing and eventually pursued design school.
  • Chesky was drawn to industrial design, which he later realized was highly relevant to running a tech company.

"I was an artist. I would be drawing and drawing, and I had these pads of paper, and I'd go through hundreds and hundreds of pages, almost compulsively drawing."

The quote reflects Chesky's early passion for art, which played a significant role in his development and future career.

The Relevance of Industrial Design to Running a Tech Company

  • Industrial design involves understanding the manufacturing process and the implications of design decisions.
  • Chesky learned to consider materials, sustainability, costs, and marketing in design.
  • He acknowledges the unexpected benefits of his design education for leading a tech company like Airbnb.

"It turns out industrial design was one of the best educations to run a tech company."

This quote reveals Chesky's realization that his background in industrial design provided a strong foundation for his role as CEO of a tech company.

The Desire to Escape and Design a Better World

  • Chesky discusses his childhood desire to escape challenges and create a better world.
  • He was inspired by Walt Disney and the concept of designing magical worlds.
  • Chesky aimed to design a world where he could fit in, as he felt different and struggled with fitting into his environment.

"I was just so obsessed with designing a world that was different and better than the one I was in."

The quote encapsulates Chesky's childhood motivation to create an alternate reality where he felt he belonged.

The Impact of Feeling Different and the Need for Belonging

  • Chesky identifies with the common feelings of not being enough and being different.
  • He relates these feelings to the human desire for connection and belonging within a tribe.
  • Chesky's work became a productive addiction that masked his need for love and connection.

"I think the core thing is I was different. I was different in almost every way. Indifferent wasn't good."

This quote underscores the challenges Chesky faced growing up feeling different and how it affected his sense of belonging.

The Psychological Cost of Success and Work Addiction

  • Chesky reflects on the personal cost of his work addiction, despite its productive outcomes.
  • He discusses the importance of purpose, health, and relationships for happiness.
  • Chesky warns that success and status won't fill internal voids and emphasizes the need for introspection and connection.

"I felt like my entire life, many people have turned to addiction. And if I turned to one was work."

The quote highlights Chesky's recognition of his work addiction as a coping mechanism for deeper emotional needs.

The Loneliness of Leadership

  • Chesky describes the unexpected loneliness that comes with successful leadership.
  • As Airbnb grew, the informal bonds with early team members evolved into formal employer-employee relationships.
  • Chesky stresses the importance of staying connected to avoid isolation and maintain good decision-making.

"Lonely leaders are probably not the best leaders."

This quote conveys the idea that loneliness can impair a leader's effectiveness and empathy.

The Importance of Maintaining Connections

  • Chesky advises entrepreneurs to actively maintain connections with friends and peers.
  • He regrets not staying in touch with important people in his life during Airbnb's growth.
  • Chesky now values relationships with both old friends and fellow entrepreneurs who understand his current experiences.

"I would keep my old friends and I would be friends of people, my situation."

The quote reflects Chesky's belief in the importance of sustaining relationships from different stages of life for a balanced perspective.

Advice to Younger Self

  • Chesky would advise his younger self to prioritize time for loved ones.
  • He discusses the paradox of people being hesitant to reach out to busy individuals.
  • Chesky emphasizes the ease yet importance of making an effort to maintain relationships.

"It's completely obvious to me that I would make time for the people I love."

This quote reveals Chesky's hindsight realization that dedicating time to loved ones should have been a priority amidst his busy schedule.

The Illusion of Perpetual Life and the Need for Urgency

  • Chesky contemplates the illusion of having unlimited time and the tendency to procrastinate.
  • He suggests imagining a limited time left to live to create a sense of urgency and focus.
  • Chesky believes in balancing long-term goals with the importance of daily connections and happiness.

"You have this decade, what would you want to do?"

The quote encourages a mindset of urgency and purposeful living, considering the finite nature of life.

The Power of Ten Years

  • Ten years is significant for personal growth and achieving goals.
  • Small ideas can become vast over a decade if one is disciplined and focused.
  • Brian Chesky reflects on his 15-year journey with Airbnb.
  • He emphasizes the importance of shared experiences with others.
  • Memories from shared experiences, like vacations, tend to be more vivid and lasting.

"If you're disciplined and focused, and you can have a small idea, a small dream, a small goal, and you can build something vast."

This quote highlights the potential of small ideas to grow into large accomplishments with discipline and focus over a period like ten years.

"And I think life is about experiences, but the best experiences are the ones you share with other people."

Chesky values shared experiences, noting that they are often the most memorable and impactful aspects of life.

Reflections on Life and Regrets

  • Brian Chesky contemplates what he would regret if he only had six minutes to live.
  • He would regret not spending more time with loved ones and not ensuring they knew how he felt about them.
  • Chesky also expresses a desire for a family, which he has not yet created.
  • Despite potential regrets, he feels gratitude for the experiences he has had and the people he has worked with.

"I think my biggest regret would be the time I didn't spend with people I love, maybe making sure those people knew how I felt about them."

Chesky identifies time not spent with loved ones as a potential major regret, emphasizing the importance of relationships in life.

"The one thing I haven't created that I've always wanted was probably a family."

This quote reveals Chesky's personal longing for a family, which he considers an important aspect of life that he has yet to achieve.

The Influence of Walt Disney and Creativity in Business

  • Chesky discusses the influence of Walt Disney's biography on his entrepreneurial journey.
  • He admires Disney and Steve Jobs for their creativity in leading tech companies.
  • Chesky applied Disney's concept of storyboarding to Airbnb's customer experience.
  • He advocates for the importance of creativity in business and questions the dominance of analytical thinking in corporate America.

"What if we created a storyboard of the perfect vacation on Airbnb from the time you book to the time you check in?"

Chesky explains how the concept of storyboarding from Disney's work inspired him to design a comprehensive customer experience for Airbnb.

"Numbers are the language of business. And I remember thinking to myself, no, language is the language of business."

This quote challenges the idea that business is solely about numbers, asserting the importance of creativity and communication in business success.

The Origin of Airbnb and the Importance of Starting Small

  • Airbnb began as a small idea to solve a personal problem.
  • Chesky stresses that most companies start small and grow over time.
  • He shares the story of how Airbnb started with airbeds and a simple idea during a conference.
  • The advice to focus on making a few people love your product rather than many just liking it is highlighted.

"It's better to have a hundred people love you than a million people that just sort of like you."

Chesky underscores the importance of cultivating a small, passionate user base as a foundation for growth and word-of-mouth marketing.

"Airbnb we did not design a way for millions of people to stay in homes. Airbnb started one weekend."

This quote illustrates how Airbnb's massive success originated from a modest and practical solution to a temporary problem.

Creativity Versus Analytical Thinking in Corporate America

  • Chesky argues that creativity should not be abandoned as a company grows.
  • He believes businesses need more creativity and heart to remain relevant and serve people.
  • The focus on short-term financial metrics can be detrimental to long-term success and innovation.
  • Chesky calls for a balance between analytical thinking and creative intuition in business leadership.

"If you think of a company like a body, most companies, it's like they're cut off at the head, they're disconnected from their heart."

Chesky uses a metaphor to describe how companies often lose touch with their creative and emotional core, which can stifle innovation.

"Not everything that counts can be counted. Not everything that can be counted counts."

This quote, attributed to Linus Pauling, is used by Chesky to argue that not all important aspects of business can be measured by numbers, and a focus solely on measurable data can lead to missed opportunities.

The Importance of Entrepreneurial Belief and Persistence

  • Entrepreneurs must believe in their vision and convince others to join their journey.
  • Rejection is a common part of the entrepreneurial experience, as illustrated by an email rejecting Airbnb's early funding request.
  • Chesky emphasizes that transformation towards one's ideals requires audacity and the ability to overcome obstacles.

"Airbnb was trying to raise $150,000 at a $1.5 million, I think post money valuation."

This quote provides context for the early financial struggles and ambitions of Airbnb, highlighting the modest beginnings of now-successful companies.

"The world doesn't just change, or at least it doesn't just transform towards our dreams, ideals and ambitions that require certain types of people."

Chesky reflects on the role of entrepreneurs and inventors in changing the world, noting that it takes special individuals to turn their dreams into reality despite challenges.

Entrepreneurial Leadership and Challenges

  • Entrepreneurship involves navigating through numerous challenges and uncertainties.
  • Leaders must motivate and push their team beyond their comfort zones, akin to a trainer urging for "three more reps."
  • The ability to invent solutions, like building a bridge to cross a stream, with limited resources is crucial.
  • Recruiting people along the journey and maintaining their morale is a key leadership trait.
  • Entrepreneurs need to handle and reformulate a multitude of divergent ideas.

"And the question is, when people are cold and they're shivering and they're not sure what to do, and you're running out of resources and rations, can you find your way up that mountain?"

This quote emphasizes the leader's role in guiding the team through adversity, making strategic decisions, and finding a path forward despite challenges.

Founder's Unique Attributes

  • Founders bring a deep passion and a sense of ownership that professional managers may lack.
  • Founders have the permission to make significant changes, like rebranding, based on their intimate knowledge of the company's origins.
  • Having built the company, founders understand its core and how to rebuild it if necessary.
  • Professional managers often do not possess the same level of attachment, permission, and foundational knowledge as founders.
  • Founders may struggle to scale their leadership as the company grows, and succession planning becomes a challenge.

"A founder brings three things that a professional manager doesn't have. The first thing a founder has is they're the biological parent."

This quote highlights the founder's inherent connection to the company, likening it to the bond between a biological parent and their child.

The Importance of Culture in Companies

  • Culture is foundational for future innovation and is considered the most important aspect to design within a company.
  • A strong culture allows a company to operate with the agility of a startup regardless of its size.
  • Culture is more than just a set of written values; it is the shared way of doing things, learned from experiences and modeled by leaders.
  • Culture influences every decision, from hiring and firing to promotions.
  • It is the ultimate intellectual property of a company, more than technology or exclusive contracts.

"Simply put, culture is what creates the foundation for all future innovation."

This quote captures the essence of company culture as the bedrock upon which all other aspects of the company are built and thrive.

Creating and Sustaining Company Culture

  • Culture is not built through mere declaration of values but by everyday actions and decisions.
  • Leaders shape culture by setting examples and constantly refining the organizational practices.
  • Culture becomes ingrained when the team internalizes the leader's standards and replicates them in the leader's absence.
  • The behaviors that define a company's culture are closely tied to its vision and personal values of its leaders.
  • A strong culture can lead to a collective consciousness, aligning the entire company towards shared goals and values.

"Your culture is the behaviors of the leaders that get mimicked all the way down, every single person."

This quote explains that culture is disseminated throughout the organization through the behaviors exhibited by leaders, which are then emulated by others.

Culture as a Response to Adversity

  • A company's culture is truly revealed in times of crisis.
  • Leaders must make principled decisions during crises, focusing on long-term reputation and values rather than immediate outcomes.
  • Crises require decisive action and consideration of all stakeholders.
  • Viewing a crisis as a defining moment can foster an optimistic mindset, which is contagious and crucial for morale.
  • The hardest aspect of managing a crisis is often the leader's own psychology.

"Whatever you do in your darkest hour, that becomes your culture, because your culture, people think, is the perks, the yoga, the free food. No culture is like when everyone said you were going to fail in your darkest hour."

This quote underscores that the true test of a company's culture is how it responds to its most challenging times, which defines its character more than any superficial perks.

Optimism and Creativity in Crisis

  • Optimism is essential as it sets the stage for creativity, especially in crisis situations.
  • Creativity is likened to finding a third path when only two undesirable options seem available.
  • During a crisis, Airbnb had to make tough decisions, including reducing the company size by 25%.

"And you damn well need creativity in a crisis, because in a crisis, you often have, like, two bad options, and you sometimes want that third path."

The quote emphasizes the importance of creativity in navigating difficult situations where conventional solutions are inadequate. It suggests that optimism can help foster the necessary creative thinking to find unconventional solutions.

Handling Company Layoffs with Compassion

  • Brian Chesky wrote a heartfelt letter to employees during layoffs, focusing on their well-being and future opportunities.
  • Airbnb provided exceptional benefits to laid-off employees, including mental health support and healthcare maintenance.
  • An alumni directory was created to help laid-off employees find new jobs, with many getting rehired through this initiative.

"We created an alumni directory where if you were laid off, you could opt into a public directory. We'd publish your information and we'd point recruiters to your information."

This quote describes the proactive steps Airbnb took to support laid-off employees, illustrating a commitment to their future success beyond the company.

Emotional Investment in Leadership

  • Brian Chesky believes that emotional involvement in leadership helps understand the full impact of decisions.
  • He reflects on the emotional difficulty of laying off employees and the importance of acknowledging their contributions.
  • The layoff letter was a defining moment for him, and it garnered gratitude from those affected, highlighting the importance of dignity and recognition even in hard times.

"I say, get as emotionally involved as possible so you understand the consequence decisions and now try to make a decision."

The quote underlines the belief that leaders should fully comprehend the emotional ramifications of their decisions, suggesting that this approach leads to more holistic and considerate decision-making.

Airbnb's Recovery and IPO Success

  • Post-layoffs, Airbnb employees worked to rebuild the company, leading to a quick recovery.
  • The company's successful IPO, valued at over $100 billion, was a moment of mixed emotions for Brian Chesky, combining pride with a sense of sadness.
  • The experience reinforced the idea that daily happiness comes from engaging in meaningful work and maintaining relationships, not from external achievements.

"And then we decide to go public. And we go public at a valuation that probably valued at 48, $50 billion. And by the time, within an hour of opening, we're $100 billion."

The quote highlights the remarkable financial turnaround and market success of Airbnb, despite the challenges faced during the pandemic.

Personal Reflections Post-IPO

  • After the IPO, Brian Chesky experienced a period of isolation and sadness, realizing that work alone could not fill the void.
  • He learned the importance of intentionally designing his personal life to include time with loved ones.
  • Chesky's reflections led to a renewed focus on personal connections and a more balanced approach to life and work.

"That's when I started reaching back out to people, and that became the beginning of everything. That changed how I felt personally."

This quote captures the transformative realization that personal connections are vital for well-being, prompting Chesky to prioritize relationships in his life.

The Future of Airbnb and Community Focus

  • Brian Chesky envisions Airbnb evolving from a service focused on spaces to a global travel community centered on people.
  • He aims to foster trust and connection through rich user profiles and personalized experiences that go beyond travel.
  • Chesky's vision includes combating loneliness and reinforcing the belief in fundamental human goodness and similarity.

"I think what I'd like everybody to become is more of a community, more of like a global travel community."

The quote outlines Chesky's aspiration for Airbnb to become a platform that cultivates a sense of community and belonging among its users worldwide.

Personal Challenges and Relationship Building

  • Despite professional success, Chesky acknowledges the challenges of forming personal relationships and the complexity of dating in his position.
  • He emphasizes the importance of being open-minded and following curiosity rather than a prescribed type in seeking romantic partners.
  • Chesky's approach to relationships mirrors his philosophy on discovering life's passions—both require active participation and openness to the unexpected.

"I think the better thing is to follow your curiosity... You must actively put yourself out there in situations to discover what you love, what you love and who you love."

This quote draws a parallel between finding one's passion and building relationships, suggesting that both pursuits involve exploration and a willingness to embrace the unknown.

Reflections on Love and Decision Making

  • Chesky feels loved and supported after sharing his experiences, realizing he was never as alone as he thought.
  • He emphasizes that love should guide decision-making, as it is a fundamental and enduring emotion that provides direction.
  • The discussion concludes with Chesky expressing gratitude for the connections he has made and the importance of expressing love openly.

"I think the most important feeling that I have is love. And I make my best decisions when I'm feeling that, because that love is like the light. It's like a true north star."

The quote conveys the idea that love is a guiding force in life, underpinning the best decisions and providing a sense of purpose and direction.

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