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

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

August 26, 2025
05:11 PM
5 min read
AI Enhanced

Key Takeaways

Despite having a massive org chart, the Airbnb CEO Brian Chesky runs his company like he’s just got started.

Article Overview

Quick insights and key information

Reading Time

5 min read

Estimated completion

Category

personal finance

Article classification

Published

August 26, 2025

05:11 PM

Source

Fortune

Original publisher

Success·EntrepreneursAirbnb CEO Brian Chesky says he’s still in founder mode—he personally handpicks staff, treats them as direct reports, and decides who staysBy Jessica CoacciBy Orianna Rosa RoyleBy Jessica CoacciSuccess FellowJessica CoacciSuccess FellowJessica Coacci is a reporting fellow at Fortune where she covers success

Prior to joining Fortune, she worked as a ducer at CNN and CNBC.SEE FULL BIOBy Orianna Rosa RoyleAssociate Editor, SuccessOrianna Rosa RoyleAssociate Editor, SuccessOrianna 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

SEE FULL BIO Despite having a massive org chart, the Airbnb CEO Brian Chesky runs his company he’s just got started

Myunggu Han--Getty imagesWhile many workers push back against micromanagement, Airbnb CEO Brian Chesky is doubling down on a hands-on apach

The $79 billion rental giant boss says he is still involved in personnel decisions for as many as 50 employees: “ hire, fire, mote, and manage.” Even Chesky admits it may sound “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 a startup—including being involved in personnel decisions for around 50 employees. “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… , hire, fire, mote, and manage.” Even Chesky admits it may sound “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 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 dered 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 ed this advice, the results were disastrous

Paul Graham, one of the most influential figures in Silicon Valley who att 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 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 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, fessionally 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 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 apach from Steve Jobs’ playbook and began removing layers of management

Other leaders have ed 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 bably play that role as well,” von Ahn said

Introducing the 2025 Fortune Global 500, the definitive ranking of the biggest companies in the world

Explore this year's list.