Airbnb CEO: “Airbnb Was Worth $100 BILLION & I Was Lonely & Deeply Sad!”

Added: Oct 9, 2023

Chesky begins by addressing the impact of the pandemic on Airbnb. He reveals that the company lost 80% of its business in just eight weeks, leading to questions about the future of Airbnb. He acknowledges the difficult decisions that had to be made during this time and shares a letter he wrote to the entire company expressing his emotions and concerns.

The conversation then shifts to Chesky's early life and how his passion for art and design shaped his identity. He describes himself as a sensitive and idealistic child who used art as a way to escape the challenges of childhood. Chesky explains that he always felt different and struggled to fit in, which fueled his desire to create a world where he could belong.

Chesky also opens up about his hyperactivity and impulsiveness as a child, noting that he was never diagnosed with ADHD but had an intense energy and a desire to do things differently. He shares his journey into industrial design school and how it taught him the importance of understanding three-dimensional design and the manufacturing process.

The conversation then delves into the loneliness and isolation that Chesky experienced as the CEO of Airbnb. He admits that he was unprepared for the emotional and psychological challenges that came with leading a successful company. Chesky emphasizes the importance of staying connected to friends and loved ones, as loneliness can hinder leadership and decision-making abilities.

Chesky reflects on the sacrifices he made for his addiction to work and the impact it had on his personal life. He realizes that seeking external validation and success does not fill the void inside and that true happiness comes from within. He encourages others to focus on purpose, health, and relationships, as these are the key elements of a fulfilling life.

The conversation then turns to the concept of time and the importance of making the most of it. Chesky regrets not spending enough time with the people he loves and not creating a family of his own. He acknowledges that life is more than just climbing the ladder of success and that true happiness comes from experiences, relationships, and purpose.

Chesky shares his perspective on the loneliness of leadership and the need to fight against isolation. He advises entrepreneurs to stay connected with friends, meet other entrepreneurs, and actively seek out human connection. He believes that loneliness can hinder empathy, resilience, and decision-making abilities.

The conversation continues with Chesky discussing the power of creativity in business. He draws inspiration from Walt Disney and Steve Jobs, who were both creative leaders in their respective industries. Chesky believes that creativity is being systematically squashed in corporate America and emphasizes the importance of empowering creative individuals to drive innovation and change.

Chesky continues by emphasizing the reliance on data in business and how it can lead to derivative and iterative thinking. While data is necessary, it is not sufficient for success. He argues that following intuition, heart, and having new ideas are equally important. He believes that as companies grow, they need to continuously refound and rebuild themselves, and that creativity and heart are essential for success.

Chesky highlights the difference between Airbnb and other large multinational corporations, stating that many companies are disconnected from their heart and focus solely on the analytical side of their brain. He believes that companies need more creativity and heart in order to serve their purpose and create a better world.

He discusses the risk-averse nature of many organizations and how they become focused on themselves rather than their purpose. He criticizes the over-reliance on short-term financial measurements and the lack of focus on long-term vision, quality, and brand. Chesky argues that companies need to embrace creativity and take risks in order to adapt to a changing world.

Chesky shares an email from 2008 in which Airbnb was rejected by an investment firm, stating that the potential market opportunity was not large enough. He contrasts this rejection with the current success of Airbnb, which handles nearly as much money as the entire GDP of Croatia. He emphasizes the importance of entrepreneurs and founders in driving change and creating wealth.

The conversation then shifts to the topic of culture. Chesky explains that culture is what creates the foundation for innovation and is the most important thing a company can design. He believes that culture is not just about values and principles, but about the shared way of doing things and the behaviors of leaders and employees. He emphasizes the importance of leading by example and constantly shaping and pruning the culture.

Chesky shares an email he recently sent to the entire company about the importance of culture and how Airbnb aims to create a culture that feels like working at a startup. He discusses the need to reimagine the HR function and focus on bringing out the best in people.

The conversation then turns to the COVID-19 pandemic and its impact on Airbnb. Chesky describes how the company faced its darkest hour when the pandemic hit and travel came to a halt. He talks about the difficult decisions they had to make, including laying off a significant number of employees. He emphasizes the importance of making principled decisions rather than purely financial ones in times of crisis.

Chesky reflects on the defining moment of the pandemic and how he rallied the company together to rebuild from the ground up. He shares a letter he wrote to the employees, expressing his gratitude and love for them and acknowledging the contributions of those who were laid off. He discusses the unexpected response he received from those who were laid off, with many expressing their gratitude and love for the company.

Chesky continues by discussing the IPO of Airbnb and the mixed emotions he felt. He expresses pride and a sense of accomplishment, but also a tinge of sadness. He reflects on how his daily life remained unchanged after the IPO, highlighting the importance of staying grounded and focused on the purpose of the company.

Chesky continues by discussing the transition of Airbnb from a private company to a public one. He acknowledges that while becoming a public CEO and generating wealth for others may seem like a significant accomplishment, it does not necessarily bring the happiness and fulfillment one might expect. He emphasizes that true fulfillment comes from doing what you love and surrounding yourself with people you love, rather than solely focusing on achievements and accumulating wealth.

The CEO then shares his personal low moment, which coincided with the COVID-19 pandemic. He explains that during the crisis, he was constantly working and felt a sense of purpose and adrenaline. However, after the company went public and the crisis subsided, he found himself with more free time and a lack of direction. This led to a period of isolation and deep sadness, as he realized the importance of connecting with loved ones and making time for personal relationships.

Chesky discusses his efforts to improve his personal life and overcome feelings of loneliness. He reflects on the progress he has made in maintaining connections with friends and prioritizing his health through regular exercise and abstaining from alcohol. However, he admits that he still struggles with finding a romantic partner and acknowledges the challenges of meeting someone when his life is structured and organized.

The conversation then shifts to the future of Airbnb and its next chapter. Chesky envisions Airbnb evolving from a service focused on providing accommodations to a global travel community centered around people. He emphasizes the importance of building a robust profile system that fosters trust and understanding among users. He envisions Airbnb as a platform that not only connects people with spaces but also connects people with each other, facilitating meaningful connections and experiences.

Chesky believes that by bringing people together, Airbnb can combat the issue of loneliness that plagues society. He references his meeting with the Minister of Loneliness in the United Kingdom and expresses his desire to use Airbnb as a tool to address this issue. He believes that by reinforcing the idea that people are fundamentally good and emphasizing our shared humanity, Airbnb can create a sense of unity and understanding among its users.