Even Chesky admits it may sound like “a lot of work, but it’s necessary”. Conventional leadership advice usually says a CEO should build a top-tier exec team and get out of the way. “That to me is absolutely not what you should do,” the rental giant boss slammed. “What you need to do is have relationships with as many people as possible in the company. You need to be as close to the people doing the work as possible.”
“The only way to do that is to skip level,” the tech billionaire said, adding that he does that by talking to those reporting into his management team. “I want to have a relationship with them.”
Chesky rationalised that it’s the only way of knowing if your executive team is doing a good job—but also ensures you’re “close to the vision.” The job of the founder is “to set the vision every day, it’s to set the pace of the company, it’s to shape it every single day.”
It’s not the first time the CEO has expressed his belief in having a start-up mentality. At a Y Combinator event in 2024, Chesky delivered a speech on the pitfalls companies face when adopting “manager mode”. He recalled “well-meaning people’ advising that he let experienced execs run Airbnb, but when he followed this advice, the results were disastrous.
Since then, Chesky has echoed the same sentiment, emphasizing that the age of artificial intelligence has ushered in a need for a more nimble business hierarchy.
“I am in that [founder] mode, but we have a number of people who could probably play that role as well,” von Ahn said.
