When Brian Chesky agreed to rent out a few air mattresses in his apartment in 2007 to help make ends meet, he and his roommate, Joe Gebbia, figured they might be onto something. Not even in their wildest dreams, though, did they expect to be launching a $30 billion dollar enterprise. Now worth over $3.8 billion dollars, it’s difficult to picture the CEO of Airbnb as a young industrial designer looking for side-hustles to come up with rent money. Ultimately, however, it was exactly that situation that inspired the idea behind Airbnb, and that continues to drive the success of the business today.


Chesky’s vision, his inspiring business philosophy, and his focus on strong and vibrant communities and company culture have enabled his and his business’ success. Further, his experiences offer other entrepreneurs insights into what makes some innovative and disruptive ideas succeed while others fail.

Bringing back trust

In an extended interview, Chesky discusses how he views his business’ success and its purpose. His business is about more than just providing accommodations for travellers. He doesn’t look at Airbnb as a brand new, ultra-progressive idea, but rather as a way to enrich cities, and to restore a lost sense of community and “village”, that went missing in the 20th century. Until relatively recently, in historical terms, people stayed in boarding houses and homes when they travelled. Hotels, by contrast, owe their dominance to a loss of trust in other people, replaced by a lesser faith in institutions and brands. Chesky aims to bring back that trust to facilitate healthier and more community oriented cities, to enable micro-entrepreneurship, and to encourage the shared use of spaces and resources.

While Chesky himself doesn’t strongly embrace the term “sharing economies” himself, his philosophy and his business are clear and commonly-cited examples of the disruptive potential that this type of peer-to-peer approach has.

Disruptive sharing

Disruptive innovations often seem obvious in retrospect, and few more so than sharing-based businesses like Airbnb. Sharing economy based businesses make sense, because they allow regular people to apply their existing resources and skills to compete in an industry that wasn’t previously accessible to laypeople. It’s not surprising that, given the opportunity, people would want to rent out a spare room, a guest house, or an empty apartment to make some extra money on the side. Airbnb started as a side hustle, and its fundamental purpose today is to enable others to do the same.

The hotel industry didn’t see this coming as a possible disruption they needed to prepare for, because they never considered that the threat was real. After all, how could an enterprising homeowner possibly market themselves more effectively than a hotel? How could they guarantee quality service?

In founding Airbnb, Chesky and his cofounders elegantly solved this issue. The platform connects micro-entrepreneurs to their customers, and includes a rating system designed to keep users honest. This allows these non or semi-professional individuals to collectively saturate markets, and to compete against established enterprises in the industry.

Building strong company cultures

While he had something going for him with a great idea and the ambition to create a more efficient, better connected, and more egalitarian world, the secret to Chesky’s success ultimately lies in the way he pursued that passion. Even a great product won’t endure, he says, if it isn’t supported by a similarly great company. This latter challenge is, according to Chesky, all about creating a strong and vibrant company culture.

Brian Chesky doesn’t believe in “good” or “bad” company cultures, so much as strong and weak ones. A weak company culture doesn’t unify its employees, or help a business connect with its customers, resulting in a weak brand. By contrast, a strong company culture helps to define an environment and experience for both employees and customers. Every strong company culture is different, and better suited to different kinds of people with different values.

Strong cultures require careful hiring

Cultures are defined by the people that operate within them. For a business, that means hiring the right people is about much more than acquiring labour resources. According to Chesky, bringing in new employees is like introducing new DNA to an organism. That DNA will cause changes in the long term, and it’s up to entrepreneurs to ensure that those changes are complementary to their vision for their company. When it came time to hire Airbnb’s first employee, Chesky personally interviewed hundreds of applicants before settling on Nick Grandy. Taking his time with that choice, and the ones that followed, may have been slower in the short term, but it allowed him to better shape the values and core identity of Airbnb.

Brian Chesky started as an industrial designer looking for a way to make rent. That initial perspective has informed his entrepreneurial approach ever since. His passion for enabling micro entrepreneurs and enriching cities, together with his insight in building a strong company culture to represent his core values has made him one of the world’s youngest billionaires, and most important entrepreneurs of the 21st century. By emulating his approach of empowering innovative ideas with strong supporting company cultures, you and your business will also be better able realise your own vision.