As the co-founder and CEO of Airbnb, Brian Chesky has navigated the company from a humble air mattress in a San Francisco apartment to a global hospitality giant. His journey has been marked by a unique, design-centric approach to leadership and a deep-seated belief in the power of culture and customer obsession. Chesky, who trained as an industrial designer, has consistently emphasized that design is not merely about aesthetics but about the fundamental way a system works—a principle he applies to both Airbnb's product and its organizational structure. His leadership was particularly tested during the COVID-19 pandemic, a crisis that brought the travel industry to a standstill and forced him to fundamentally rethink the company's focus and operations. Through it all, he has emerged as a thought leader on stakeholder-centric capitalism, long-term vision, and the importance of a hands-on, founder-led approach to building a company.
On Unique Leadership Style & "Founder Mode"
- "Great leadership is not absence; great leadership is presence."[1][2][3] This quote encapsulates Chesky's belief in a hands-on leadership approach, which he has termed "founder mode."
- "The general principle is being in the details and being very hands-on."[1] He advocates for leaders to be deeply involved in the specifics of the product and the business.
- "I think a lot more leaders would benefit from being in the details and model more hands-on leadership."[1] Chesky challenges the conventional wisdom that leaders should always delegate and avoid the details.
- "Being in the details is what every responsible company's board does to the CEO."[4] He argues that if it's responsible for a board to be in the details, it's also responsible for a CEO to do the same with their team.
- "There's a difference between micromanagement which is like telling people exactly what to do and being in the details."[4] For Chesky, being in the details is about partnership and shared understanding, not dictatorial control.
- "Every decision should be our decision."[1] This mindset fosters a collaborative environment where leaders and their teams work through problems together.
- "I think the psychology of the leader becomes the psychology of the organization."[5][6] Chesky emphasizes the leader's role in setting the emotional and psychological tone for the entire company.
- "Today is your most courageous moment."[7] He believes that the present is always the best time to make bold decisions, as the pressures will only increase with time and scale.
- "I stopped apologizing for how I wanted to run the company."[5][8] The pandemic served as a crucible moment for Chesky, giving him the conviction to lead in a way that was authentic to his design background.
- "The biggest gift a leader can give to a person is to believe in them."[6] This can manifest as both praise and pushing people to achieve more than they thought possible.
On Management and Company Culture
- "Culture is a thousand things, a thousand times. It’s living the core values when you hire; when you write an email; when you are working on a project; when you are walking in the hall." This quote, while not in the provided search results, is a widely attributed and fundamental Chesky belief on the pervasive nature of culture.
- "Culture and brand are two sides of the same coin."[9] The internal beliefs and principles of a company will inevitably shape its external promise and identity.
- "In a high trust organization, then I can just tell you do the right thing...you can move really fast."[10] A strong culture built on shared values allows for greater autonomy and speed, as opposed to a low-trust environment bogged down by rules and manuals.
- "Your brand evangelists are your employees."[9] Passionate employees are the foundation for creating a strong brand and a loyal customer base.
- "Every leader should be an expert in what they're leading."[4] He argues against the idea of "people managers" whose sole responsibility is managing people without deep domain expertise.
- "Five teams should do one thing rather than one team do five things."[4] This is a call for focus and a reduction in the number of concurrent projects to increase impact.
- "What everyone really wants is clarity. What everyone really wants is to be able to row in the same direction really quickly."[4] Chesky believes that autonomy without clear direction leads to misery, not happiness.
- "We want to hire people that are here for our mission."[11] He stresses the importance of hiring people who are motivated by the company's purpose, not just perks or valuation.
- "The best way to slow a project down is to add more people to it."[4] This reflects his philosophy of maintaining a lean and efficient team structure.
- "Your job is to focus on anything below this waterline, anything that can sink the ship."[10] An advisor's metaphor that Chesky adopted, focusing his attention on foundational areas like culture that are critical to the company's survival.
On Running the Company and Strategy
- "Measure success by decades not quarters."[12] A core tenet of his business philosophy is to prioritize long-term vision over short-term financial gains.
- "Consider all stakeholders not just short-term investors."[12] This belief places hosts, guests, employees, and communities on equal footing with shareholders.
- "Bad companies are destroyed by a crisis. Good companies survive a crisis. But great companies are defined by a crisis."[6] Quoting Andy Grove, this became a mantra for Chesky during the pandemic, viewing it as a defining moment for Airbnb.
- "When you're our size, and the business drops by 80% in eight weeks, it's is like being in an 18-wheeler going 80 miles-an-hour, and then you slam on the brakes."[13] A vivid description of the initial shock of the COVID-19 pandemic on Airbnb's business.
- "The hardest thing to manage in a crisis is your own psychology."[5][13] He learned that a leader's optimism, rooted in reality, is crucial for fostering the creativity needed to navigate a crisis.
- "It’s better to have 100 people love you than a million people that sort of like you."[11] A lesson from Y Combinator's Paul Graham that shaped Airbnb's early focus on building a passionate user base.
- "The best marketing is investing in the user experience. And then your users will market for you."[11] This philosophy emphasizes product excellence over traditional advertising.
- "Why does your company deserve to exist?"[14] A question Chesky asks other entrepreneurs to force them to articulate their unique contribution and purpose.
- "I want Airbnb to be the company that gets you off your phone."[14] A forward-looking statement on the company's mission to foster real-world human connection.
- "We rebuilt the company from the ground up."[8][15] The pandemic forced a fundamental restructuring of Airbnb, moving from a divisional to a functional organization and ruthlessly prioritizing projects.
On the Importance of Design
- "Design is not just how something looks; it's how it fundamentally works."[16][17] Echoing Steve Jobs, Chesky's core design philosophy is about the entirety of the system, from the business model to the organizational chart.
- "We approach everything at Airbnb through a design lens."[8] This statement underscores the centrality of design thinking in every aspect of the company.
- "Running a company in a design-led way actually is good for business."[18] Chesky argues that creativity and commercial success are not mutually exclusive.
- "You can live in a world of your own design, you can change the world, you can redesign it."[11][17] A lesson from his time at the Rhode Island School of Design (RISD) that profoundly shaped his worldview.
- "Product managers are critical, but they shouldn't be doing the job of a designer."[16] He advocates for a partnership where designers are helping to drive the product, not just executing on a product manager's vision.
- "If you don't want to put your name on it, you don't ship it."[15][16] A simple but powerful rule he instituted to elevate the quality and pride in the work being produced.
- "The problem with five stars is the only reason you would leave less than five stars is because it was horrible... the bar to do five stars is really low."[17] This observation led to his famous "11-star experience" thought experiment, pushing the team to imagine what a truly magical, beyond-expectations experience could be.
- "Design is kind of a solution to uncertainty ultimately."[8] In uncertain times, he believes that having a clear vision of what you want to build is a powerful antidote.
- "If people love our products, they're going to want to buy more of them."[16] A straightforward justification for the business value of a design-led approach.
- "A lot of businesses need more heart and more imagination."[16] Design, for Chesky, is a way to inject these essential human qualities into a company.
Other Foundational Learnings
- "When you're starting a company, the difference between being an entrepreneur and unemployed is kind of a state of mind."[19] A humorous but insightful reflection on the uncertainty and self-belief required in the early days of a startup.
- "Starting a company is like jumping off a cliff and assembling the airplane on the way down."[20] A vivid metaphor for the chaotic and creative process of entrepreneurship.
- "Don't apologize for how you want to run the company because when you are in your darkest moments, the principles in who you are is what you have to lean on."[21] A lesson in authenticity and conviction, especially during challenging times.
- "If you think you're going to have more courage tomorrow than you do today, you're going to have a lot more pressure tomorrow than you do today."[7] A powerful argument for decisiveness and taking action in the present moment.
- "Dogma is the death of being an entrepreneur."[7] Chesky advocates for first-principles thinking rather than blindly following established conventions.
- "The key is that, it's not that creativity should drive everything. It's that it should be in the room. It should be in the conversation."[18] A nuanced view on the role of creativity in a business context.
- "I saw potential in people that they didn't see in themselves."[6] This highlights his role as a leader in pushing his team to achieve their full potential.
- "I don't think I want society to be led by a bunch of lonely people."[20] A poignant reflection on the importance of connection and relationships for leaders, noting that lonely leaders are often less trusting and empathetic.
- "We still love to build, and it turns out that we really are changing the world."[5] A statement that captures the enduring passion for creation and impact that drives him.
- "Our core competency has to be we have to be willing to change and not be viewed as static."[11] In a world defined by technology and change, the ability to evolve is paramount.
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