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Bold Leader Spotlight – Brian Chesky, Co-Founder and CEO of Airbnb

brian chesky airbnb leadership

Brian Chesky is not your typical tech startup CEO. In fact, he began studying architecture and attaining a degree in industrial design. But today, Chesky is well recognized as the bold Airbnb leadership figure. The global peer-to-peer lodging service provides accommodations for over two million guests each night. So, it’s only natural to wonder how one of the youngest CEOs became the face of Airbnb leadership.

Having been listed among Fortune Magazine’s top 20 of the World’s Greatest Leaders, Chesky is certainly intriguing. In addition to his dynamic personality, Chesky has unique insights on what it means to be a bold leader. Guts, determination, perseverance and an ability to change allowed him to excel as Airbnb leadership grew in the market.  Humility, values, and a collaborative approach similarly showcase his bold leadership talents. His Airbnb leadership approach is a major reason the company continues to thrive. As per Ed Kopko’s book, “Project Bold Life: The Proven Formula for Taking on Challenges and Achieving Happiness and Success”, “Pursuing boldness in our lives demands seeking a higher level of excellence.” Chesky certainly sought a higher level of excellence, and it shows in his achievements.

brian chesky airbnb leadership
For the Airbnb CEO, the excitement in business is in “getting there”. 

Leveraging Unique Experiences to Challenge the Status Quo

Chesky and Joe Gebbia, another cofounder, first came up with the idea that led to Airbnb in 2007. They shared an apartment in San Francisco where the Industrial Designer Society of America was holding its convention. Short on rent, and realizing all the hotels were completely booked, they had an idea. They bought three air mattresses for their place and rented out each for $80 a night. Thus, the idea of “air bed and breakfast” was born.

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The two officially began working on their idea in 2008 and soon added the company’s third cofounder, Nathan Blecharczyk. Getting traction, however, was difficult. Selling their idea was a challenge to venture capitalists for a few reasons. For one, no one trusted an architectural designer to launch the next big unicorn. Likewise, no one bought into the idea that a person would want to live in someone else’s home. But Chesky and his colleagues knew they were onto something because of their unique experience. It was this single unique circumstance that led to Airbnb leadership internationally.

brian chesky shares airbnb leadership style
There’s more to humility than just being a virtue. It does actually solve problems.

Humility and a Willingness to Guide Others

One of the greatest aspects of Chesky’s bold leadership is his continued humility as the Airbnb leadership figure. Early in the course, Chesky sought out anyone who might offer advice for success. One of those pieces of advice came from Y Combinator’s Paul Graham. He encouraged Chesky to get to know every single one of his customers. While that would be impossible today, in 2008 this was more feasible. So Chesky and his other Airbnb leadership team flew between New York and California and did just that.

These early experiences taught Chesky a great deal about bold leadership. By being humble, he was able to gain insights he would not otherwise have gained. Likewise, he has continued to use humility in dealing with various company conflicts. Specifically, issues that have arisen with landlords and city governments are being approached with a desire to understand. And Chesky himself seeks opportunities to lecture and mentor other entrepreneurs of the future. Airbnb leadership would not have enjoyed the same level of success without this important component.

brian chesky speaks about mentoring
When you think someone like Brian Chesky doesn’t need any more mentoring, he emphasizes how gaining knowledge from accomplished entrepreneurs is very important.

Value-Driven Airbnb Leadership Focused on Community Empowerment

Some of the criticisms of Airbnb relate to its effect on long-term housing in some urban markets. But at the same time, Chesky has sought to empower communities rather than undermine them. Specifically, a key reason for the Airbnb leadership position in the market is its effect on social ecosystems. Hundreds of struggling communities are now seeing tourism and an influx of commerce resulting from Airbnb travelers. In fact, it’s estimated the Airbnb ecosystem has generated over $60 billion for these communities and over 1.3 million jobs.

Chesky has always been about values and contributing to society. Indeed, the original idea sought to solve a key problem…insufficient rent money. But at the same time, the service met a concurrent community need as well. Chesky continues to see himself in this role by striving to create a product that’s both likable and sustainable. This value-driven Airbnb leadership approach epitomizes Chesky’s focus as a community and social leader.

brian chesky on being a community leader
Brian Chesky built a tribe, not a product.

Brian Chesky, Continuing to Grow as a Bold Leader

In 2015, Time Magazine recognized Chesky as one of the top 100 Most Influential People. In 2016, Forbes Magazine identified Chesky as one of the richest entrepreneurs under 40 years of age. These are just two of the many accolades Chesky has received for his bold leadership abilities. And certainly, he deserves these awards because of the kind of Airbnb leadership, which inspires so many people.

But Chesky isn’t done yet as he continues to guide the company in new directions taking on new challenges. In addition to being quite comfortable with change, Chesky embraces his desire to learn and grow. This explains not only why Airbnb leadership in the hotel market continues. It also accounts for its expansion into Airbnb experiences and other unique ventures. All of these bold leadership traits show why Brian Chesky is among the best CEO’s in the world today. And it will likely be the reason Airbnb may very well excel in areas we have yet to consider.

a cartoon of brian chesky of airbnb - a global peer-to-peer lodging service
Bold Leader Brian Chesky has a value-driven Airbnb leadership focused on community empowerment.

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