Airbnb’s CEO studied Steve Jobs’s playbook to slash bureaucracy and build his $84 billion empire

On a recent episode of The Verge’s “Decoder” podcast, the 43-year-old entrepreneur doubled down on the “founder mode” managerial approach he helped to popularize, 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,” he said. “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.”

Officially coined by Y Combinator founder Paul Graham, founder mode isn’t just limited to chief executives. Chesky argues the philosophy can be applied to leadership in government, nonprofits, and coaching, emphasizing a need for hands-on management through presence and collaboration, not control.

“If you want to just get something going, you need to get everyone organized,” Chesky said. “But [getting] everyone organized has a multi-year roadmap, so they now need to make room on the roadmap.”

Chesky is no stranger to nimble teams, famously transforming a tiny San Francisco apartment and three inflatable air mattresses with his fellow cofounders into a Fortune 500 giant with an $84 billion market cap. While the short-term rental behemoth now rakes in well over $11 billion a year, the company’s early iterations weren’t always conducive to rapid growth. 

“To me, so many roads lead back to the conversation we have with org charts and founder mode, because you don’t want to miss the next wave,” Chesky said. 

Brian Chesky’s “founder mode” strategy

Chesky credits founder mode with helping to save a flailing Airbnb during its early years. 

In an October 2024 interview at the “The Art of Hiring” event hosted by Ramp, Chesky described the early stages of his company as a “matrix” with no limits on the numerous layers of management. Teams formed sub-teams, which formed their own sub-teams, and so on, each adding to a bloated structure with office politics, lack of accountability, and complacency. 

“You end up with a lot of bureaucracy,” Chesky said. “You end up with a company where there are meetings about meetings, where metrics and strategic priorities are the only things that bind the company together.”

It’s a “soul crushing” lesson Chesky experienced first-hand when Airbnb’s plans to go public collided with a wave of global financial turmoil and sweeping shutdowns caused by the COVID-19 pandemic, an unprecedented crisis that threatened to jeopardize the company’s future. 

“We went from the hottest IPO since Uber and Alibaba to people asking, ‘Is this the end of Airbnb?’” Chesky recalled. 

At the onset of the COVID-19 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. To adapt, the company laid off 25% of staff and paused non-core operations. 

To save his flailing company, 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.” 

Emulating Apple founder Steve Jobs’ playbook, Chesky began to systematically eliminate layers of management, removing managers who weren’t deeply involved in the work, and only selecting highly skilled “experts” to lead key functions instead. 

“You can be deeply involved without telling people what to do,” Chesky said. “It’s about working through problems with them.” 

This strategy paid off. The business ultimately went public in December 2020 with a $100 billion valuation, the year’s largest. In 2022, Airbnb netted its first profitable year with $8.4 billion in revenue, and it officially joined the Fortune 500 ranks the next year, in 2023. 

Chesky, now in his 18th year at the helm of the short-term rental giant, continues to innovate, recently announcing new features in May that allow guests to book experiences like spa treatments, personal training, and in-home meals from professional chefs in addition to their stays. 

Airbnb’s winning hiring strategy 

In his 2024 conversation at “The Art of Hiring” event, Chesky also offered five tips for how to find the best new recruits. 

1.  Start with the results

Chesky believes leaders should focus on impact, not titles on résumés, to build the best teams. 

“[Hiring managers] start with the brands. Oh, this person worked at Google. But you should actually ask yourself, what products do I admire? Then, who built those products?” Chesky said. “It’s like a detective novel to actually find out who actually did the thing.”

Fellow Fortune 500 CEO Jamie Dimon agrees, suggesting chief executives “open our horizons” to employees from more diverse backgrounds. 

“The new world of work is about skills, not necessarily degrees,” Dimon said in the 2024 documentary Untapped. “We must remove the stigma of a community college and career education, look for opportunities to upskill or reskill workers.”

2.  Be a detective

In order to find the best workers, Chesky emphasizes the need to be “detective” and rely heavily on reference checks. For Chesky, it’s not enough for a candidate to say they were involved in a successful campaign or product, they should prove their contribution to the outcome, too. 

“I remember Andreessen Horowitz would tell me, you should do eight hours of reference checks per employee, which is probably over the top,” Chesky said. “But you should probably spend as much time referencing as you do hiring.”

3.  Ask better questions and dig deep

Chesky recommends kicking off a reference call by assuring the conversation is off the record to elicit more honest responses, and asks for specific examples to back up the praise.

“What do I need to watch out for if I were to hire them? What is the one area of development you would give them?” Chesky said. “If you say that, they have to tell you something because they feel like they’re not thoughtful enough.”

4.  Recruit beyond openings

Chesky said networking is central not just to hiring, but to long-term success. At the end of each reference call, he asks for two additional candidate suggestions.

It’s a strategy that can be applied for job seekers, too. According to a recent survey from LinkedIn, over a third of Gen Z workers feel anxious about networking due to isolation during the COVID-19 pandemic, and feel they don’t know how to begin.

“Hiring is too much like a sales pipeline, and hiring should be more like network building than a sales pipeline,” Chesky said.

5.  Dig deeper in interviews

For a successful interview, Chesky suggests hiring managers ask follow-up questions—ideally, two in a row—to move past surface-level answers. 

“You never want to get the first answer. You always want the third answer, and if people don’t know what they’re talking about, they struggle,” Chesky said. “They might be able to follow up, but in the second follow-up, they actually become absent of details.”