The CEO Moment: Airbnb’s Brian Chesky

In twenty years, Airbnb has transformed from a few air mattresses on an apartment floor to a well-known American technology company. Brian Chesky, 45, has been its leader throughout this evolution. At a time when Silicon Valley isn't known for introspection, Chesky stands out as someone who frequently examines his own character. He admitted that his primary weakness as a founder was having to pay for his immaturity in his thirties. However, he believed it was a good long-term bet.

Chesky is one of three founders who started the company in 2007. Out of many founders leading Fortune 500 companies, he finds that founders tend to be more detail-oriented, decisive, and bigger in their authority. They are more likely to take bold risks because they have the moral authority to do so. For example, he could change the name of the company, even though a professional manager would feel it's not theirs to change.

Chesky has criticized the traditional way companies approach hiring. He believes it should be around 50% of a CEO's job, which he thinks is not the case in practice. He also doubts the value of remote work policies that are easy to explain as they might be one size fits all. Chesky thinks that leaders don't need to have regular one-on-one meetings with their direct reports, and most great CEOs do not have them.

Despite being vocal about not needing regular one-on-ones, Chesky started Airbnb because he was ideologically against hotels. He wanted to offer an alternative to hotels. However, in 2018, when customers demanded hotels, he had to make a decision on whether to include them or not. He realized that there were three types of people: those who only book Airbnbs, those who only book hotels, and most people who are willing to book both.

Chesky sees the new initiatives around housing as part of Airbnb's solution to the problem of making cities more expensive. He is creating a $250 million fund to help with the last dollar of completion for stalled housing development projects. Chesky also plans to open source data around cities, policies, and the cost of living to help cities with the best policies lower housing costs.