From Air Mattresses to a Global Movement: How Brian Chesky’s Vision Built Airbnb

In 2008, Brian Chesky stood at a crossroads with his friends Joe Gebbia and Nathan Blecharczyk.

Struggling to pay rent in their San Francisco apartment, they devised a creative plan: why not offer a spot to sleep for attendees of an upcoming design conference?

They placed air mattresses in their living room and called it “Air Bed and Breakfast,” offering something affordable and personal for guests looking to avoid expensive hotels.

This simple solution soon became Airbnb, a platform where people could share their homes with travelers around the world.

Yet, getting Airbnb off the ground was anything but easy. Investors initially turned them away, doubting the idea of people sleeping in strangers’ homes.

Chesky and his co-founders had to find another way to fund their dream. Instead of giving up, they decided to sell something unusual: cereal.

In 2008, during the presidential election, they created limited-edition boxes of “Obama O’s” and “Cap’n McCain” cereal.

This unexpected product sold well, raising $30,000 that they put directly back into Airbnb. It was a bold move, demonstrating Chesky’s determination and ability to think creatively under pressure.

Chesky knew that convincing people to stay in others’ homes required a deep sense of trust. Travelers needed reassurance, and so did hosts. Chesky and his team worked hard to make Airbnb a safe and trustworthy community.

They introduced identity verification, guest reviews, and a generous host guarantee for property damage. With each added measure, Airbnb’s reputation grew, turning wary customers into loyal users who felt safe embracing this new way of travel.

As Airbnb gained popularity, Chesky’s leadership faced an unexpected test—the COVID-19 pandemic. Almost overnight, travel plummeted, and with it, Airbnb’s revenue. Tough decisions followed, including the painful choice to lay off a quarter of the workforce.

Chesky focused on Airbnb’s core mission of “belonging anywhere” and kept his attention on the safety of hosts and travelers.

He pivoted the company’s offerings toward local travel and long-term stays, positioning Airbnb to adapt to a world with new restrictions. Under Chesky’s guidance, Airbnb not only survived the pandemic but found new ways to thrive.

Chesky’s vision for Airbnb went beyond lodging; he wanted it to foster genuine connection. He emphasized belonging, not just booking. From this foundation, Airbnb created “Airbnb Experiences,” letting travelers connect with hosts through curated experiences that celebrated local cultures. Even as the company scaled, Chesky held tight to his vision of making the world feel a little closer.

With resilience and a clear long-term view, Chesky led Airbnb through regulatory challenges, economic downturns, and public scrutiny, eventually taking the company public in 2020. His approach kept Airbnb from being just another travel company—it became a resilient, transformative force in the industry.

Central to Chesky’s success was his people-first leadership style. Hosts, he believed, were the heart of Airbnb. He made it a priority to equip them with tools and resources, building a community of empowered hosts rather than a simple marketplace. Chesky’s dedication to empowering his team and his hosts created a culture of partnership and trust.

As a leader, Chesky embraced empathy, accountability, and integrity, always treating his team, hosts, and guests with respect. His leadership built a culture where accountability and compassion drove decisions, which not only strengthened Airbnb’s brand but deeply resonated with millions of users worldwide.

Under Chesky’s vision, Airbnb grew from a small experiment into a global community, fundamentally changing how people travel and connect. It wasn’t just a new business model—it was a new way of seeing the world, all led by a man who believed in sharing and belonging.

Chesky’s leadership approach to the 7E Leadership Model

1. Ethics

Chesky’s actions, especially his emphasis on transparency and creating a culture of trust, align closely with the ethics principle. For example, he worked directly with hosts and guests, even staying in properties himself, to understand and address concerns. This transparency in understanding customer pain points built trust within the Airbnb community and reinforced Airbnb’s values.

2. Envisioning

Chesky had a clear vision to “create a world where anyone can belong anywhere,” which went beyond simple travel accommodations. His commitment to this vision inspired his team to rally around the idea of belonging and community, unifying them under a shared goal. This vision also guided strategic choices, even in moments of uncertainty, which kept the company aligned with long-term growth.

3. Endurance

During Airbnb’s early days, Chesky showed remarkable resilience, pivoting strategies and staying focused through financial struggles and investor rejection. His creativity in selling branded cereals to fund the company exemplifies his endurance and ability to view challenges as opportunities, inspiring his team to persevere and grow together.

4. Excellence

Chesky’s Approach: Chesky’s dedication to customer experience reflects his pursuit of excellence. By focusing on improving Airbnb’s platform to ensure safety and transparency, Chesky not only created a better user experience but also drove the team to strive for higher standards in service. His disciplined focus on refining Airbnb’s mission and vision helped the team achieve a world-class product.

5. Encouragement

Chesky fostered an inclusive, collaborative environment by hiring people who aligned with Airbnb’s core values and encouraging open communication. His leadership style emphasized team empowerment, which helped Airbnb attract talent who were motivated and aligned with its mission. Chesky’s actions to understand different perspectives also inspired a strong sense of unity and purpose among employees.

6. Enablement

Chesky enabled his team by providing them with the freedom to make decisions that would benefit Airbnb’s growth. By actively seeking mentorship himself and encouraging a learning culture, Chesky supported an environment where creativity and independence flourished. His empowerment of team members cultivated an adaptable workforce ready to innovate in a dynamic environment.

7. Effectiveness

Rather than seeking immediate profits, Chesky focused on building Airbnb into a platform that prioritized trust and long-term value. His commitment to creating a lasting brand demonstrated a keen focus on effectiveness. Chesky’s decisions around trust-building and customer-centric improvements showed a commitment to Airbnb’s long-term success and the broader impact on community-building in the travel industry.

Through these 7E leadership skills, Chesky's approach shaped Airbnb into a resilient, customer-focused, and visionary organization that transformed the travel industry by focusing on a balance of ethics, endurance, and effectiveness.