Brian Chesky’s new blueprint for Airbnb — and Silicon Valley

“When I came to Silicon Valley, we thought we were all making the world a better place,” Brian Chesky recalls, 19 years after he co-founded Airbnb. Now, he tells The CEO Signal, “Silicon Valley’s in a bubble, and society feels like AI is happening to them, not for them.”

Chesky is an unusual figure in California’s tech heartland. An industrial designer surrounded by mathematicians and engineers, he describes Silicon Valley as a nightclub he somehow snuck into as a 26-year-old when the bouncer wasn’t looking.

“I wasn’t supposed to be here,” he says. But he has grown close to CEOs like OpenAI’s Sam Altman, and he thinks he can help the AI industry’s leaders understand what people who stay in Airbnbs really think of them.

The aesthetic Chesky honed at the Rhode Island School of Design permeates his San Francisco headquarters, a former Eveready battery factory whose meeting rooms look like Airbnb rentals from around the world. But he implies that other pioneers around him have lost sight of who they’re designing their products for. Tech executives love talking in lofty terms about “humanity,” he says, but his fellow founders should be talking about people — like school teachers and mill workers — and listening to them, too.

“I talked to one famous person — I won’t mention who — and I said, ‘Do you talk to a regular person?’ He goes, ‘Yes, such and such.’ I’m like, ‘Well, that’s your nanny,’” Chesky says. “We should talk to normal people we don’t pay, people who are willing to tell us to F off and tell us why they don’t like us.”

A $250 million pitch to get on ‘the right side’ of the housing issue

Chesky has had plenty of blunt feedback as Airbnb has grown, with cities from New York to Barcelona blaming his company for making housing less affordable. Despite years of engaging with local politicians, Airbnb has failed to stop some of them from implementing caps or outright bans on short-term rentals.

Asked whether he has any responsibility for the housing affordability crisis, Chesky replies: “I think we have a responsibility. I think there’s a difference between having responsibility and being the primary cause.”

Listings on Airbnb typically comprise just 0.5% of the housing stock in cities where it operates, he says, and many of those properties are primary or second homes someone is already living in, rather than units that have been removed from the long-term rental market. Bans on short-term rentals haven’t reversed housing inflation in cities like New York, he notes.

The bigger issue, Chesky argues, is a shortage of new construction. Last month, Airbnb positioned itself as a partner in solving that problem by announcing a $250 million fund to provide “last-dollar” financing for housing projects with funding shortfalls. It’s a small sum for a company with a $100 billion-plus market capitalization, but he says it should unlock an additional $5 billion of new housing.

“It’s not philanthropy,” he says. Airbnb will make a return — albeit a smaller one than some real estate investors would expect — “but we’re also going to be on the right side of this issue.”

Even so, he says, concerns about housing affordability are only going to get “much worse” as more people want to move to cities. The two biggest issues in the 2028 US presidential election, he predicts, will be affordability and AI.

Chesky’s advice for AI’s ‘Promethean moment’

Chesky says he does not believe that AI will destroy humanity any time soon, but he thinks society is unprepared for the technological power that has been unleashed in this “Promethean moment.” Technology used to feel like a train that people just had to jump on to “ride into the promised land of progress,” he says. “And now people feel like they’re [on] the train tracks, and the train called AI is coming for them.” 

Silicon Valley cannot credibly police AI, he believes, warning his peers that if the technology is left unregulated, “bad sh*t is going to happen, and there’s going to be overcorrection, and then there’s going to be a hammer coming down.”

Nor does he believe that Washington can regulate AI successfully, because policymakers don’t understand the technology well enough. “Bridge-builders” between Silicon Valley, Washington, and ordinary people are needed — and he is putting himself forward as one of them.

One of his recommendations, he says, is that AI founders should stop talking about impossible-sounding goals like “saving humanity.” Instead, they should take on one issue at a time, starting with the most immediate problem AI has exacerbated — cybersecurity. In the meantime, Silicon Valley is “losing people because we’re not talking about people,” he warns. “We just need to put design principles and humanity into AI.”

A new mission in matchmaking

Even as Chesky critiques Silicon Valley’s blind spots, he is using them to define a new ambition for Airbnb.

Innovations like e-commerce and online banking mean that people are spending more time on their devices and less time bumping into friends and strangers in shopping malls, banks, and “the real world,” he observes. Even our on-screen lives are more isolating than they were, he adds, since tech companies have rejected the form of social networking that was filled with updates from our friends for more advertiser-friendly social media. AI’s potential to fuel isolation is far greater, Chesky believes, saying that this may be “the loneliest time in human history.”

His hope is that Airbnb can “use a device to get you off a device.” And he’s not just talking about customers using its app to book a room in a stranger’s house, or sign up for one of the add-on experiences that Airbnb has been encouraging hosts to offer, like cooking lessons or sightseeing tours.

“If my mission was to basically mainstream sleeping at a home instead of a hotel, then I’m done,” he says. Instead, he has “a higher purpose, a higher calling” in mind.

What Airbnb has built is not a booking engine but “a system of trust,” he says. The 290-odd million users and 5.5 million hosts whose identities it has verified represent “a real-world social graph,” Chesky believes, which opens up a new opportunity in “matchmaking.”

He won’t reveal the details of what that means until next year, but he is talking about helping people find roommates and long-term property rentals, or integrate into new communities. And those product ideas are wrapped in a bigger ambition.

“One of the things that makes for a really good culture and mission is that you don’t just stand for something; you stand against something. Great cultures kind of need enemies,” Chesky says. The hotel industry was a natural foe for Airbnb in its early days, but Chesky has revised that “ideological” enmity and begun to strike deals with boutique and independent hotels. Now he is thinking about defining his company in opposition to something bigger. “Maybe the enemy should be loneliness.”

Making the case for micromanaging

This is not the first time that Chesky has talked of a new beginning for his company. Two years ago, the Y Combinator co-founder Paul Graham held him up as a prime example of the hands-on leadership style he called “founder mode.”

The background was Chesky’s response to an 80% collapse in Airbnb’s business over the early weeks of the pandemic. He restructured the company, scrapping divisions and removing layers of management. Then he recast his own role as “editor-in-chief,” reviewing every product in detail before Airbnb released it to users and working alongside people several levels below him.

Chesky does not shy from describing his approach as micromanaging, and admits that he faced “huge pushback” from people who felt disempowered and feared that he would slow the company down.

But it gave him a firsthand understanding of “who was good and what was not good in the company,” and helped him ensure that everyone was “rowing in one direction.” Diving into the details of his employees’ work lets him fix their bad habits, he says, but people don’t need to be micromanaged forever. “Like a golf instructor, you’ve got to watch their swing, and eventually you can let go.”

Why Airbnb’s founder became its chief recruiter

Chesky thinks he was born a good founder. Convincing people that his ideas were important enough to work on together came easily to him, he explains. But learning how to run a company was another matter.

“Most people can’t be a good CEO and no one starts [as] a good CEO,” he says, mentioning Steve Jobs’ rocky first tenure at Apple. He has had to learn how to lead, he says, starting with a total overhaul of his approach to personnel.

If Chesky were starting a new business today, his first hire would be a recruiter, he says. He once treated hiring as a chore, he says, but since shifting into “founder mode,” he has spent two to three hours each day hiring people.

“The No. 1 thing a CEO does is recruit talent,” he says, adding that he has learned from years of fixing rushed personnel decisions that “the more time I spend recruiting, the less time I have to spend managing.”

Chesky has made himself “co-hiring manager” not just for positions in his executive team but for their direct reports, too, which means he gets involved in interviews for openings in Airbnb’s top 200 roles. His reasoning is that he wants that second tier of leaders, who may end up as candidates for positions in his top team, “to feel a direct connection to me,” the founder, rather than to other executives, who might move on. “They have to be my people, not just their people.”

Chesky is looking for more than loyalty, he says. “If you join for the executive, you’re joining for the Airbnb of today. But if you join for me, you’re joining for the dream of tomorrow,” he explains. And that attracts a more ambitious kind of candidate, he thinks. “You’re not just joining a short-term rental company. You’re joining a company combating loneliness.”