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Leadership Lessons from Airbnb Co-Founder, Brian Chesky

There hasn’t been a lot of start-ups in the recent years to showcase the kind of growth trajectory as done by Airbnb, the unique online home-sharing platform. It took the company less than 9 years to transform itself: from being a ‘crackpot’ idea, it went on to become a major disruptor in the global hospitality industry. Today, it enjoys a private market worth close to $30 billion.

Brian Chesky is one of the three co-founders of Airbnb; he never attended a formal business school. Yet, he took on the leadership role while his partners, Nathan Blecharczyk and Joe Gebbia, focused on the design and technology aspects of the new home-renting business that they were about to launch. In 2008, Airbnb made its debut as Airbedandbreakfast.com and today, it has over 21 offices across the globe.

Of course, the success of Airbnb didn’t come easy. Here’s what Brian Chesky has to offer to all budding entrepreneurs looking to become successful leaders in the future.

  • It is critical to believe in an idea in order for it to work

Brian says that his idea was initially dismissed by nearly all investors. They deemed it as ‘crazy’ and he had to fight to keep the startup afloat. But what really helped was the fact that he and his partners were absolutely convinced about the idea and knew they would figure out a way to make this work. In 2008, the three men even went out to sell breakfast cereal boxes with funny names to those attending the Democratic National Convention, in order to keep the business going.

  • Make curiosity your biggest ally and be shameless in seeking help

Even though Chesky had zero entrepreneurial experience, he took on the challenge and became shameless in seeking advice and guidance from top leaders in the industry. His mentor network included people like Mark Zuckerberg, Jeff Weiner, Marc Andreessen, and Reid Hoffman. Chesky believes that even though he was fortunate to have these boldfaced names to guide him, it is possible to find helpful sources no matter where you stand. The only thing needed is a desire to venture out and ‘ask’ for mentorship.

  • Step into the shoes of your customer to learn

Airbnb is a company that has always focused on getting loyal customers, rather than getting a lot of customers. In the year 2011, the organization was working to strengthen its customer services. For this process to be successful, Chesky went out to live in over 30 different locations listed on Airbnb. He says that when he used his own services, he was better able to figure out which areas needed polishing.

  • Dig in to know all the rules and regulations for your industry

It’s true that Airbnb has had to face multiple issues with regards to national and local hospitality laws. Some of the problems were inevitable because the technology startup was forced to work with legislation that rejected the budding concept of a sharing economy. According to Chesky, the only way to deal with such industry hurdles is to gain a lot of knowledge and to embrace open-mindedness. He believes that it is absolutely possible to operate in harmony with the local and national laws.

The biggest lesson: Airbnb’s first encounter with major controversy

It was in 2011 that Airbnb had to face its first client horror story. A renter had destroyed a woman’s house in San Francisco and taken off with her valuables when she was away for business. The victim had used her personal blog to make this story public and it went viral in no time. The media, of course, was eagerly awaiting Airbnb CEO Brian Chesky’s response.

This crisis caused Chesky to learn his most important leadership lesson thus far. Weeks after the disaster, Brian finally wrote something on the Airbnb blog. He said that he had reached a point where his priorities had completely changed. He came to the conclusion that he needed to stop obsessing with the outcome and keep the focus on the principle.

Brian’s blog said that the company had experienced a sort of paralysis following the news of the disaster and the team believed that they had screwed up pretty bad. The response should have been more prompt and communication more sensitive. The woman needed reassurance and the company should have offered her that instead of a simple apology. However, the company was unprepared to face such a crisis and the ball was naturally dropped.

To take things in control, Brian made an announcement that Airbnb would give a sum of $50,000 to all renters in protection. This guarantee was announced by Chesky against the advice given within the organization to first conduct a testing. 

According to Chesky, the frustration and embarrassment that came with the disastrous experience taught him his greatest lesson as a leader. In a crisis, a universal decision will usually land you somewhere in the middle of a road. These are typically the most horrible decisions. A crisis calls for either going right or left.

This decision of Chesky earned him a lot of respect and applause from the entire industry, including other veteran leaders.

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