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How I Built This

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

When COVID hit and Airbnb lost 80% of its business, Brian was forced to rethink everything he knew about leadership.

Brian CheskyguestGuy Razhost

Nov 2, 20261h 5mWatch on YouTube

Summaries, chapters, transcripts, and FAQs on this page are made by uListen, not YouTube.

CHAPTERS

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Chapter summaries

IPO aftermath: success, Zoom celebrations, and a surprising loneliness
Brian Chesky describes waking up the day after Airbnb’s IPO to an oddly normal, isolated pandemic routine. The lack of in-person celebration and the quick fade of the “rush” triggered an inner crisis about what success actually changes. He reflects on ambition driven by validation and the realization that reaching the “mountaintop” doesn’t automatically bring happiness.
- •The IPO experience felt surreal and anticlimactic because it happened over Zoom during the pandemic
- •He went from the high of becoming CEO of a massive public company to waking up alone and returning to routine meetings
- •He describes ambition tied to wanting to be “special” and seeking adulation that wears off quickly
- •Reaching a major goal led to questions about purpose: what he wants out of life and why he’s doing any of it
From art school identity to building a business model (and getting comfortable with money)
Guy Raz and Chesky revisit Chesky’s background at the Rhode Island School of Design and the early sense that he wasn’t destined for conventional success. Chesky explains how the culture of art school shaped his initial resistance to monetization and how he later embraced the practicality of building a business model. He frames his trajectory as unlikely—an artist who “snuck into” Silicon Valley.
- •He recalls a pivotal graduation-night conversation where Joe predicted they’d start a company and people would write about it
- •Chesky shares family and personal signals of insecurity about success, including his yearbook quote
- •He describes RISD’s culture of artistic “purity” and how he initially opposed focusing on making money
- •He explains how the team ultimately designed a business model that proved extremely strong, and how his views on capitalism shifted
Early leadership limits: believing he could lead small, not scale
Chesky explains that he initially saw himself as a leader of only a handful of people, even while believing the idea could become huge. Guy Raz frames the early Airbnb years as a steep learning curve: two designers in a tech ecosystem learning how to hire and manage. Chesky sets up the distinction between being a natural founder and struggling as a CEO.
- •He believed he could lead at a small scale, even if he could imagine Airbnb becoming massive
- •The founding team’s background as designers shaped how they navigated a tech-centric environment
- •Early-stage leadership required learning basics of hiring, management, and directing work
- •He positions the coming challenges as moving from “founder instincts” to “CEO responsibilities”
“Great founder, terrible CEO”: the counterintuitive job of running a company
Chesky argues that founding can feel intuitive because it resembles making and building from childhood, while being a CEO is counterintuitive and learned later. He challenges common leadership advice—especially for young companies—and emphasizes the difficulty of building culture and alignment. He describes the real challenge as ensuring people do the right things when the CEO isn’t in the room.
- •He says people may effectively ‘practice’ being founders for years, but not being CEOs
- •He critiques early-stage advice to hire very experienced people and get out of their way, calling it dangerous for young companies
- •He stresses staying close to the company early and hiring people only slightly ahead who are hungry and adaptable
- •He frames the CEO role as creating alignment, culture, and direction—not just managing profitability or expenses
When experience clashes with intuition: deference, people-pleasing, and conflict avoidance
Chesky recounts being intimidated by older, experienced hires and deferring to them even when his instincts disagreed. He describes being conflict-averse, avoiding hard conversations, and sometimes compensating by doing others’ jobs for them. He also explains how failing to say no can splinter a leadership team into competing directions that create long-lasting organizational consequences.
- •He often deferred to experienced hires to avoid seeming arrogant, and later viewed that as a frequent mistake
- •He describes himself as a people pleaser who wanted older, more experienced colleagues to like him
- •He avoided difficult performance conversations, hoping problems would resolve themselves
- •He emphasizes the CEO’s role in saying no and choosing one direction for the company rather than allowing multiple competing paths
Imposter thoughts and chaos years: feeling trapped, learning curve limits, and why he stayed
Chesky shares that he frequently wondered if he was the right person to lead and felt stuck in a ‘prison’ of responsibility. He believed the company couldn’t grow faster than his learning curve and tried adding presidents/COOs without lasting success. He attributes his persistence to his father’s “never quit” mindset and to continued belief from his co-founders and board.
- •He regularly questioned whether he was the right CEO and felt trapped by the role
- •He believed a company’s growth is limited by the CEO’s learning curve
- •He describes mid-to-late 2010s growth alongside organizational chaos—meetings about meetings and scattered direction
- •He stayed due to a deep personal aversion to quitting and because co-founders and the board continued to back him
Loneliness as the hidden leadership problem: identity blur and learning vulnerability
Chesky explains how the CEO role became isolating as the company matured and social dynamics changed. He describes losing personal identity—becoming “the Airbnb guy”—and how that made him less effective as a leader. He connects loneliness to a lack of vulnerability and not letting people in, especially during pandemic isolation.
- •He contrasts the camaraderie of early co-founding with the isolation of being CEO as employees’ lives change
- •He describes feeling constantly watched and evaluated, making leadership feel like a performance
- •He says his identity blurred with the company, leaving him with little to talk about beyond Airbnb
- •He links loneliness to being closed off and unwilling to admit uncertainty or ask for help
Mentorship from Barack Obama and rebuilding a personal life (trust, friends, and “concentric circles”)
Chesky recounts writing to Barack Obama for help and being told the core issue was loneliness, with a focus on staying connected to long-term roots. He describes rebuilding friendships through Zooms and trips, and learning a framework for loneliness described by the U.S. Surgeon General. He explains choosing a default of trust—accepting risk of betrayal as preferable to isolation—while watching how people treat others.
- •He says Barack Obama advised staying grounded by staying connected to people from one’s roots
- •He restarted relationships with high school and college friends and created shared experiences through travel
- •He relays a “concentric circles” model of connection: self, close relationships, confidants, community, and a larger sense of belonging
- •He chose to give people the benefit of the doubt while using cues like how they treat assistants to judge character
How Airbnb got “stretched and sprawling”: hubris, abundance, and adolescence of a company
Chesky reflects that the company expanded into too many directions not primarily due to investor pressure, but due to hubris after early success. He describes forgetting how hard the core product was to build, throwing resources at new bets without rigor, and the organizational dysfunction that followed. He argues that dysfunctional complexity can tempt leaders to step back, when presence is what’s needed.
- •He attributes overexpansion to believing that because one thing worked, everything else would be easy
- •He says the company grew and started new initiatives without sufficient structure, leadership, or discipline
- •He describes adolescence-like growing pains: bureaucracy, diluted focus, and constant reorganizations
- •He argues that in dysfunction, leadership presence matters more than absence
The COVID shock as a crucible: 80% business loss and a shift into hands-on leadership
Chesky describes the pandemic as a life-or-death moment that forced him to become the kind of CEO the company needed. He recounts a board member warning of massive travel impact and Airbnb losing 80% of business in weeks. He says the crisis compelled him to get deeply involved, cut projects, simplify, and make hard calls—then keep operating that way afterward.
- •He recalls being warned the pandemic would dwarf prior travel crises and then losing 80% of business quickly
- •He frames the moment as the first time he truly had to be a great CEO to ensure survival
- •He says he discovered he performs well in crisis and rose to the stakes
- •He chose not to revert to pre-crisis operating habits after stabilizing the business
Studying Steve Jobs and building “founder mode”: simplify, say no, and set the bar for excellence
Chesky explains how learning from people who worked closely with Steve Jobs pushed him to study how Jobs pulled Apple back from near failure. He adopted a model of intense attention to detail, simplification, and ruthless prioritization to drive excellence. He describes using deep involvement to teach standards—like iterating a press release dozens of times—until quality becomes “muscle memory.”
- •He began studying Jobs specifically to understand how to recover from near-bankruptcy and crisis
- •He emphasizes simplifying, cutting projects, making hard decisions, and maintaining exacting standards
- •He describes deep involvement as a way to teach quality and alignment, not just to control outcomes
- •He explains that once standards become habitual, a leader can let go more sustainably while still seeing enough
Skip-level leadership and empowerment vs. autonomy: friction with execs and a new operating system
Chesky describes changing his information flow by talking two or three layers down and assembling full chains of command for key projects. He acknowledges the friction this caused—executives feeling undermined and accusations of micromanagement—and says much of the executive team eventually left. He distinguishes empowerment (clearing the path, resourcing, fast decisions) from autonomy over direction, arguing direction must stay aligned.
- •He adopted skip-level conversations to avoid relying only on direct reports for information
- •He put full chains of command in the room so decisions could be made with context and speed
- •He says executives objected and many eventually left as the company shifted operating style
- •He draws a line between empowerment and autonomy: people can own execution, but direction must remain coordinated
Keeping dissent alive: truth-tellers, asking for opinions first, and deliberately inviting pushback
Chesky explains how he tries to ensure people can challenge him despite strong opinions and a clear vision. He describes relying on long-tenured “truth-tellers” and people who aren’t afraid of losing the job, and shares techniques like withholding his opinion until others speak. He also describes taking the opposing position to create oxygen for disagreement, using a company tagline debate as an example.
- •He values a core set of long-tenured people who will tell him the truth
- •He says it helps to have some colleagues who don’t feel financially dependent on the role and can speak freely
- •He often asks others’ opinions before sharing his own to avoid biasing the room
- •He sometimes reverses his stance to explicitly grant permission to disagree and test comfort with dissent
Airbnb’s next chapters: reconsidering loyalty programs and committing to Airbnb.org’s crisis housing scale
Chesky describes becoming less ideological over time, revisiting ideas he once rejected—like advertising, hotels, and loyalty programs—while insisting Airbnb wouldn’t copy a standard approach. He then details Airbnb.org’s long development, from an early 2008 email through disaster response and refugee support, and outlines categories like disasters, medical stays, and domestic violence. He explains deciding to pursue a goal of one million free nights per year and the internal debate about doing it responsibly as a public company.
- •He recounts reversing earlier positions on advertising and hotels, and says loyalty is being reconsidered in an original way
- •He traces Airbnb.org from an early concept through Hurricane Sandy responses and evolving disaster support
- •He cites large-scale efforts for refugees and disaster relief, and describes expanding to medical stays and support for domestic violence victims
- •He explains the ambition to scale to one million free nights per year and his belief that doing good can also be good business
What he wants long-term: creating until the end, redefining motivation, and separating luck from earned skill
Chesky reflects on whether he can imagine leaving Airbnb and answers by describing heroes who worked until the last week of their lives. He says he’s no longer motivated by adulation or money, but by love of creating and building, and hopes to keep making new friends and staying “childlike” in curiosity. He distinguishes luck as “getting the shot” from the hard work of developing skill once he had the opportunity.
- •He says he hopes to keep working on things he loves for as long as it makes sense
- •He emphasizes family as most important at the end of life while still wanting to remain engaged in creation
- •He says his motivation has shifted away from validation and money toward craft, building, and ideas
- •He frames luck as getting the chance, and effort as the training and work that followed

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