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Airbnb CEO Brian Chesky says he’s still in founder mode—he personally handpicks staff, treats them as direct reports, and decides who stays

By
Jessica Coacci
Jessica Coacci
and
Orianna Rosa Royle
Orianna Rosa Royle
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By
Jessica Coacci
Jessica Coacci
and
Orianna Rosa Royle
Orianna Rosa Royle
Down Arrow Button Icon
August 26, 2025, 1:11 PM ET
Brian Chesky
Despite having a massive org chart, the Airbnb CEO Brian Chesky runs his company like he’s just got started. Myunggu Han--Getty images
  • While many workers push back against micromanagement, Airbnb CEO Brian Chesky is doubling down on a hands-on approach. The $79 billion rental giant boss says he is still involved in personnel decisions for as many as 50 employees: “Like hire, fire, promote, and manage.” Even Chesky admits it may sound like “a lot of work, but it’s necessary”.

Airbnb may be a globally recognized, $79 billion company with around 7,300 employees, but CEO Brian Chesky says he still manages it like a startup—including being involved in personnel decisions for around 50 employees. 

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“I treat them all as my directs,” Chesky said on an episode of the Social Radars podcast on Saturday. “I skip level, I co-hire them, and I make decisions on whether or not they’re working out and leave the company… Like, hire, fire, promote, and manage.”

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.” 

Chesky doubles down on ‘founder mode’

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. 

Paul Graham, one of the most influential figures in Silicon Valley who attended the talk, published an essay describing Chesky’s style after that pivotal realisation as “founder mode.”

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. 

“In the age of AI, my argument is you need to be founder-oriented/founder mode, because you’re going to need to be able to move like a startup to be able to adapt,” Chesky previously said in June on an episode of The Verge’s “Decoder” podcast. “I think these big, professionally managed companies aren’t organized to be able to do that, so they don’t bode well for this new world.”

Wider adoption of “founder mode” 

Chesky adopted a strategy for “founder mode” after its plans to go public were disrupted by the COVID-19 pandemic.  At the onset of the pandemic, Airbnb faced a decline of 72% in revenue due to a drop in bookings and listings as the global tourism industry suffered from lockdowns. The company was forced to lay off 25% of staff.

The founder sought business advice from an old friend, famed Apple designer Jony Ive, who suggested, “You don’t manage people. You manage people through the work.” 

It was after that conversation that he adopted an approach from Steve Jobs’ playbook and began removing layers of management.

Other business leaders have followed a similar mantra: Duolingo’s CEO Luis von Ahn said in 2024 he has a “view of everything” at the language learning platform company valued at $15 billion. Other executives, such as the vice president and chief design officer, do as well. 

“I am in that [founder] mode, but we have a number of people who could probably play that role as well,” von Ahn said.

Join us for a virtual Fortune 500 Europe C-suite conversation, in partnership with Syndio, on mastering workforce decisions and pay transparency in the age of AI. Built for global and regional HR leaders, this session, moderated by Fortune editor Francesca Cassidy, will take place Wednesday, March 25, at 2:30 p.m. GMT (10:30 a.m. EDT) and feature senior HR leaders from Hilton and Syndio. Together we'll explore how CHROs are using AI to drive smarter pay decisions, manage regulatory risk, and strengthen workforce trust. Register now.
About the Authors
By Jessica CoacciSuccess Fellow

Jessica Coacci is a reporting fellow at Fortune where she covers success. Prior to joining Fortune, she worked as a producer at CNN and CNBC.

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Orianna Rosa Royle
By Orianna Rosa RoyleAssociate Editor, Success
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Orianna Rosa Royle is the Success associate editor at Fortune, overseeing careers, leadership, and company culture coverage. She was previously the senior reporter at Management Today, Britain's longest-running publication for CEOs. 

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