Airbnb CEO Brian Chesky: “I Was a Great Founder and a Terrible CEO”

Guy Raz begins with Airbnb’s December 10, 2020 IPO, when the company ended the day valued above $100 billion. Because of the pandemic, Brian Chesky celebrated through Zoom rather than with employees, friends, and family. He went to bed as CEO of a public company and woke up in an empty house, put on sweatpants, and joined a routine meeting. The achievement produced a brief rush, followed by the realization that his life and happiness had barely changed. Chesky says much of his ambition came from wanting to feel special and receive adulation, which became addictive. Reaching the mountaintop forced him to ask what he actually wanted from life.

Chesky recalls meeting Joe Gebbia at the Rhode Island School of Design, where Gebbia told him over pizza at Antonio’s that they would someday start a company and that a book would be written about it. Chesky says Gebbia saw something in him before he saw it himself. The son of social workers, Chesky had never run a company or studied business; his high-school yearbook quote was, “I’m sure I’ll amount to nothing.” At RISD, making money was considered uncool, and he initially resisted having a business model. He eventually accepted that Airbnb needed one, helping design what became a highly effective internet business model.

Chesky says he was “naturally a great founder” but “naturally a terrible CEO.” He believes founding felt intuitive because he and Gebbia had spent decades making things, selling things, and experimenting from childhood onward. Being CEO was different: conventional advice told him to hire excellent people, trust them, and get out of their way, but he argues that this can be a death sentence for a young company. Early startups need people only slightly ahead of the founders who are smart, hungry, and close to the work. The difficult CEO tasks were creating alignment, setting culture, saying no, and ensuring people moved in one direction.

As Airbnb grew, Chesky hired executives much older and more experienced than he was, then usually deferred when their experience conflicted with his intuition. He was intimidated, conflict-averse, and eager to be liked, so he avoided difficult conversations with people who were not succeeding and sometimes did their jobs for them. He also allowed executives to take the company in separate directions; years later, some would leave after building teams around those paths, leaving Airbnb to repair the consequences. Chesky describes the company in the mid-to-late 2010s as growing amid meetings about meetings, too many yeses, and insufficient alignment. He often wondered whether he was capable of being CEO.

Chesky says his father taught him never to quit, repeating, “It’s not the size of the dog in the fight. It’s the size of the fight in the dog.” His co-founders and board also continued to believe in him, including during Airbnb’s darkest periods. Yet the CEO role became isolating: unlike the early founder years, he could no longer casually socialize with employees or rely only on his co-founders. He compared becoming CEO to being made principal of one’s own high school while everyone watched. During the pandemic he worked 100 hours a week without leaving home, and his identity blurred into “the Airbnb guy.”

Chesky wrote to Barack Obama for help, and Obama identified the problem as loneliness. Obama told him he stayed grounded by remaining connected to his roots and maintaining roughly 15 friends he could call without explaining his entire life. Chesky realized that many of his own friendships had become dormant. He resumed contact with high-school and college friends, began taking trips with them instead of merely discussing the past on Zoom, and became more vulnerable with colleagues. He also learned from the U.S. Surgeon General that loneliness involves disconnection from concentric circles: oneself, family, close confidants, community, and something larger. Chesky had been disconnected from nearly all of them.

Asked why Airbnb became stretched and sprawling, Chesky rejects the idea that it was mainly investor or employee pressure. He says early success created hubris: Airbnb took off within roughly a year and a half, so its founders assumed everything else would be equally easy. They had iterated about 30 versions of the website to make the original business work, but then funded new teams as if another Airbnb would emerge automatically. Chesky says the company lacked the foundation, leaders, and discipline needed to grow the core business while starting new ones. Abundance of money replaced constraints, and Airbnb became adolescent: bureaucratic, diluted, and directionless.

When COVID hit, Airbnb lost 80% of its business in eight weeks. Board member Ken Chenault, who had led American Express through 9/11 and the 2008 crisis, warned Chesky that the travel impact could be ten times larger than 9/11. Chesky says this was the first time being a good CEO was not merely desirable: either he led well and the company survived, or it died. Maturity and 12 years of experience had made him more decisive and less impulsive, but the crisis supplied the stakes that forced him to act. His board and co-founders supported him, while he viewed the moment as only the first chapter of Airbnb’s story.

After COVID, Chesky studied how Steve Jobs rescued Apple from a near-bankruptcy situation, drawing on conversations with Apple figures Hiroki Asai and Jony Ive. He concluded that Jobs simplified the company, cut projects, made hard decisions, stayed present, and paid attention to details rather than delegating everything. Chesky applied that approach during Airbnb’s crisis by reviewing expenses and working in the details with employees. When executives later asked him to back off, he refused, saying the old approach had produced chaos. He began skip-leveling—speaking with people two or three layers below his direct reports—to obtain information unfiltered by the executive chain. Nearly the entire executive team eventually left.

Chesky says he now joins key projects from beginning to end, setting a clear vision, assigning responsibility, ensuring resources, and establishing regular check-ins. He may work on a project daily, weekly, biweekly, or monthly, but he does not remain in every detail forever. He compares the process to a golf instructor correcting a swing until excellence becomes muscle memory. One press release went through 70 versions so employees could see the expected standard; once that standard was learned, Chesky could review later work quickly. He calls the model empowerment rather than autonomy: employees control how they work, but the company must agree on which direction to pursue.

To prevent his authority from silencing disagreement, Chesky relies on longtime colleagues who can tell him the truth, asks for opinions before giving his own, and sometimes takes the opposing position. When he became convinced Airbnb had found a new tagline, he later gave his creative team two weeks to prove a better one; they returned saying the original was right. He also asks, “What’s my blind spot?” and expects to be overruled occasionally. Chesky says Airbnb is reconsidering positions he once treated as ideological: advertising, hotels, and loyalty programs. It bought HotelsTonight and is exploring an original loyalty offering, while retaining its focus on a distinctive product.

Chesky traces Airbnb.org to a 2008 email about “airbnb.org” and a 2012 response to Hurricane Sandy, when a host offered free accommodation to evacuees. The nonprofit later housed 20,000 Afghan refugees, 100,000 people displaced by Russia’s invasion of Ukraine, and provided 70,000 free nights after the Los Angeles fires. It also supports medical stays and housing for domestic-violence survivors. Chesky says Airbnb.org now responds to about 170 disasters a year. After learning that scaling to one million free nights annually would cost roughly $500 million, he and the company concluded it could be responsible to shareholders and useful to society. They plan to reach that level within five years.

Chesky says the opportunity to build Airbnb involved luck—many equally talented people never get their chance—but developing the skills to continue did not. He does not expect to stop working simply because he becomes wealthy or reaches a certain age. His heroes, including Leonardo da Vinci, Steve Jobs, Walt Disney, Sam Walton, Frank Lloyd Wright, and Picasso, kept creating late in life; he quotes Picasso saying the challenge is remaining an artist after growing up. Chesky hopes to stay “childlike, not childish,” make at least one new friend each year, and keep improving Airbnb or building something else. He says he is painting on a giant canvas and does not want to stop.