RESOLVING THE LEDGER
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Airbnb CEO Brian Chesky has never left “founder mode.” He prioritizes developing trust, attention to detail, and organization. And in the age of AI, he argues companies need to keep that mentality and move more like startups to succeed.
“The winners of AI are going to be the companies that embrace transformation,” Chesky told CNBC last week. “You might call it founder mode, not manager mode.”
Chesky has long argued CEOs should stay focused on the details. Now, with AI writing 60% of Airbnb’s new code and speeding up product development, he sees it as a way of keeping his Fortune 500 giant moving like a startup.
Chesky embodies founder mode when closely monitoring Airbnb employees’ progress on its AI initiatives, token usage, and overall output of the AI. This attention to detail is what allows the company to pioneer the rise of consumer AI platforms.
“AI is the best thing to ever happen to Airbnb,” Chesky told investors on its most recent earnings call on Aug. 6. “Today, we’re building, testing, and iterating faster than we could just a year ago.”
Earlier this year, Chesky told investors AI helped to ship new improvements faster and reduce time from concept to launch by as much as 60%. Now, fresh off a second-quarter earnings beat with $3.6 billion in revenue, Chesky said he’s planning to spend even more on AI tokens this year in a push to become an “AI-native company.”
During the earnings call , Chesky pointed to greater efficiency with its AI-powered customer service tool that resolved 45% of user inquiries without human intervention. He also revealed the company plans to test AI search.
“AI is accelerating this work across search, sign-up, checkout, and payments,” he said. “By reducing friction across the guest journey, we are converting more traffic into bookings, and that’s become one of the biggest drivers of our growth.”
Founder mode, not manager mode
Founder mode took the internet by storm in 2024 when Y Combinator cofounder Paul Graham published an essay dismantling conventional Silicon Valley management, inspired by Chesky’s talk at an event the fund hosted earlier that year.
“When I started Airbnb, I was a founder. I ran it the way a founder runs the company,” Chesky told Fortune’s Ruth Umoh a few months later. “I was in the details. I knew everything going on. I was the chief product officer of the company.”
But as Airbnb grew into the $110 billion giant it’s known as today, Chesky has evolved his leadership style, delegating more and trusting his team to carry his ideas to the finish line.
“We should start in the details, develop trust, develop muscle memory, and then let go,” Chesky said. “Great leadership is presence, not absence.”
Today, Airbnb has about 8,200 employees, but Chesky still manages the company like a small startup.
“It’s such a fallacy in modern corporate America,” Chesky said of running companies like autonomous structures. ”Companies are organizations, organization quite literally means we organize people to work together.”
Chesky isn’t the only CEO-founder in the Fortune 500: Dell Technologies , BlackRock , Meta , and Nvidia are just some of the companies still led by their visionaries. According to Fortune’s calculations, 26 of the 2026 Fortune 500 companies were founder-led.
Chesky’s newest AI venture
Chesky is so bullish on the possibilities with AI he’s launching his own lab. While details are still scarce, Chesky is excited about the possibilities of what the tech can bring both him and consumers.
“I think we’re in the beginning of a thousand-year journey on AI, so to speak,” Chesky said in a recent interview with Yahoo Finance . “I think we’ve barely scratched the surface of what’s possible with AI.”
In the meantime, Chesky is in the process of transforming Airbnb into a one-stop shop for everything needed for travel and vacationing, potentially raising the company’s revenue by $1 billion, sources close to the matter told Bloomberg .
“There’s been very little progress on consumer AI,” Chesky said. “I think the current construction of agents has been pretty limited. And I think that’s why daily life hasn’t really you’re going to see a renaissance around consumer AI that is going to begin to change daily life.”
Chesky predicted it could take up to 18 months for the new AI software to debut, admitting the journey will be a “very, very tall mountain.” The future of vacation planning lies on AI chatbot technology, according to Chesky.
“I think a year from now, you’re going to see it be very AI-native,” Chesky said. “I can’t speak for the rest of the industry, but I would assume that they’re all going to have to follow.”
This story was originally featured on Fortune.com
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