Podcasts > The Diary Of A CEO with Steven Bartlett > CEO Diaries: Airbnb’s Founder Brian Chesky on Brutal Rejection, Great Leadership, and The Biggest Mistake Founders Make!

CEO Diaries: Airbnb’s Founder Brian Chesky on Brutal Rejection, Great Leadership, and The Biggest Mistake Founders Make!

By Steven Bartlett

In this episode of The Diary Of A CEO, Airbnb founder Brian Chesky shares insights from his journey as a founder and CEO. He discusses the early challenges of raising funds for Airbnb—which now handles finances on par with Croatia's GDP—and describes how entrepreneurs must constantly develop solutions while maintaining team morale through setbacks.

Chesky explains the advantages founders have over professional managers, including their deep personal connection to their companies and willingness to implement major changes. He also addresses the role of company culture, describing it as Airbnb's core intellectual property that connects people, resources, and strategy. Chesky details how culture manifests in daily behaviors and decision-making, comparing its maintenance to gardening.

CEO Diaries: Airbnb’s Founder Brian Chesky on Brutal Rejection, Great Leadership, and The Biggest Mistake Founders Make!

This is a preview of the Shortform summary of the May 28, 2025 episode of the The Diary Of A CEO with Steven Bartlett

Sign up for Shortform to access the whole episode summary along with additional materials like counterarguments and context.

CEO Diaries: Airbnb’s Founder Brian Chesky on Brutal Rejection, Great Leadership, and The Biggest Mistake Founders Make!

1-Page Summary

Entrepreneurship and Startup Challenges

Brian Chesky, Airbnb's founder, shares his experiences with early funding challenges. Despite Airbnb now handling finances comparable to Croatia's GDP, Chesky recalls struggling to raise just $150,000 at a $1.5 million valuation in the company's early days. He describes entrepreneurship as a journey filled with unexpected obstacles, where founders must constantly invent solutions and maintain team morale even when facing setbacks.

The Unique Dynamics of Founder-Led Companies

Chesky identifies three key advantages that founders have over professional managers. First, founders possess a deep personal connection to their companies, similar to a parent-child relationship. Second, they're more willing to implement significant changes that managers might hesitate to make. Third, founders understand their company's inner workings intimately, enabling effective course correction when needed.

However, Chesky acknowledges that most founders face challenges scaling their leadership as companies grow, often necessitating a transition to professional management to ensure long-term sustainability.

The Importance of Company Culture and Team-Building

According to Chesky, company culture manifests in daily behaviors and decision-making, not just stated values. He emphasizes that leaders must actively shape and reinforce desired behaviors, comparing culture maintenance to gardening. At Airbnb, Chesky aims to preserve startup-like energy and collaboration even as the company grows globally, viewing culture as the "ultimate intellectual property" that binds people, resources, and strategy together.

1-Page Summary

Additional Materials

Counterarguments

  • Founders' deep personal connection to their companies can sometimes lead to biased decision-making and resistance to necessary change.
  • Willingness to implement significant changes can be a double-edged sword, potentially leading to instability or strategic missteps if not carefully considered.
  • Intimate understanding of a company's inner workings doesn't always translate to effective leadership or strategic vision, especially in rapidly changing industries.
  • The transition to professional management can bring fresh perspectives and expertise that a founder-led company may lack, which can be crucial for scaling and adapting to new challenges.
  • Company culture, while important, is not the only factor in a company's success; market forces, innovation, and operational efficiency are also critical.
  • Actively shaping and reinforcing company culture can sometimes lead to a lack of diversity in thought, which could stifle innovation.
  • Preserving startup-like energy and collaboration can be challenging and may not always be suitable as a company matures and requires more structured processes.
  • Viewing culture as the "ultimate intellectual property" might overlook the tangible assets and intellectual property that can be more directly linked to a company's competitive advantage and financial success.

Actionables

  • You can simulate startup challenges by creating a "Setback Simulation" game with friends or colleagues to practice resilience and problem-solving. Gather a group and invent a fictional business scenario, then introduce random setbacks like funding issues or market changes. Work together to brainstorm creative solutions, which will help you develop a mindset for overcoming real-life business obstacles.
  • Develop a personal "Culture Codex" by writing down the values and behaviors you want to embody in your daily life. Think about the qualities that make up your ideal personal culture, such as integrity, innovation, or collaboration. Regularly review and update your codex to ensure your actions align with these values, much like maintaining a company culture.
  • Practice "Micro-Mentoring" by offering or seeking short, focused mentoring sessions on specific skills or knowledge areas. This can be done with peers or professionals in your network and is akin to preserving the collaborative energy of a startup. These sessions can be as brief as a coffee break but should aim to transfer valuable insights, fostering a culture of continuous learning and support.

Get access to the context and additional materials

So you can understand the full picture and form your own opinion.
Get access for free
CEO Diaries: Airbnb’s Founder Brian Chesky on Brutal Rejection, Great Leadership, and The Biggest Mistake Founders Make!

Entrepreneurship and Startup Challenges

Entrepreneurship encompasses various difficulties, of which funding is a significant piece. Brian Chesky, Airbnb's founder, discusses his own experiences with funding issues and the broader challenges that entrepreneurs face.

Airbnb's Funding Issues Highlight Founders' Investor Challenges

Airbnb, now handling almost as much money as Croatia's GDP, faced considerable struggles in its initial phase, particularly when it came to raising funds.

Despite Later Handling Nearly as Much Money as Croatia's Gdp, Airbnb Struggled to Raise $150,000 At a $1.5 Million Valuation

Brian Chesky recounts the early days of Airbnb when they were seeking $150,000 at a $1.5 million post-money valuation. At that time, raising even that amount was a struggle for the now globally recognized company.

Entrepreneurs Must Overcome Obstacles and Push Teams Outside Comfort Zones to Achieve Goals

Being an entrepreneur means encountering and overcoming a series of challenges.

Founders Face Daunting Setbacks, Needing To Reinvent Solutions and Recruit Support

Chesky shares that the entrepreneurial journey is fraught with challenges, like cold times and obstacles that appear as unexpected pitfalls. Entrepreneurs often find themselves having to invent solutions—akin to building bridges to get across stre ...

Here’s what you’ll find in our full summary

Registered users get access to the Full Podcast Summary and Additional Materials. It’s easy and free!
Start your free trial today

Entrepreneurship and Startup Challenges

Additional Materials

Clarifications

  • The comparison of Airbnb's funding to Croatia's GDP highlights the significant financial scale the company operates on. Croatia's GDP is used as a reference point to emphasize the substantial amount of money involved in Airbnb's operations. This comparison showcases the immense growth and financial success achieved by Airbnb over the years.
  • Post-money valuation is a term used in finance to determine the value of a company after external financing or investment has been added to its balance sheet. It reflects the company's total value, including the new investment. This valuation is crucial for investors to understand the true worth of their stake in the company. It helps in assessing the dilution of existing shareholders' ownership due to the new investment.
  • To sustain team morale by focusing on the end goal means consistently reminding the team of the ultimate objective or vision they are working towards ...

Counterarguments

  • While Airbnb's early funding struggles are highlighted, it's important to note that not all startups face the same level of difficulty in raising funds, and some may secure investments more easily due to various factors such as industry, connections, or timing.
  • The narrative that entrepreneurs must constantly overcome obstacles can overshadow the fact that some successful ventures may experience a smoother path due to market conditions, existing demand, or innovative business models that face less resistance.
  • The idea that founders need to reinvent solutions may not always hold true, as sometimes adopting existing, proven solutions can be more efficient and less risky.
  • Pushing teams outside their comfort zones is not always the best strategy; in some cases, it can lead to burnout or high turnover. A balan ...

Get access to the context and additional materials

So you can understand the full picture and form your own opinion.
Get access for free
CEO Diaries: Airbnb’s Founder Brian Chesky on Brutal Rejection, Great Leadership, and The Biggest Mistake Founders Make!

The Unique Dynamics of Founder-Led Companies

Brian Chesky, a founder himself, shares valuable insights into what sets founder-led companies apart from those run by professional managers, addressing both the strengths founders bring and the challenges they face as their companies grow and evolve.

Founders Have Three Advantages Over Managers

Chesky reflects on how the inherent qualities of founders can benefit the companies they start in ways that traditional managers may not be able to replicate.

Founders' Personal Connection and Passion for Their Company

According to Chesky, founders have a profound personal connection and passion for their companies, akin to the emotional bond of a parent to a child. This profound attachment gives founders a unique perspective and motivation that professional managers might lack. Chesky emphasizes that this love for the company can be a significant advantage, offering founders a powerful source of motivation compared to hired managers.

Founders Make Changes Managers Hesitate to Implement

Chesky suggests that founders often have the authority and willingness to make large-scale changes that managers may be hesitant to undertake. Much like parents feel they have the right to guide their child's path, founders feel empowered to take risks and pivot their company's direction if needed. Part of this includes the freedom to make bold moves such as renaming or rebranding—a sentiment reflecting the level of control and commitment founders have regarding their ventures.

Founders Can Rebuild or Course-Correct the Company, Understanding Every Aspect of Its Construction

While Chesky’s point was not fully elaborated on in his transcript, he begins to indicate that founders have an intimate understanding of their company's structure and history, which enables them to rebuild or course-correct effectively. Founders know the intricacies of their companies—sometimes referred to as the "freezing temperature of a company"—which assists them in making informed decisions that might be beyond the scope of external managers.

Most Founders Can't Scale to Lead Giants, Creating Succession Challenges Due to Mortality

Chesky acknowledges that the qualities that make a great entrepreneur are not always the same that ...

Here’s what you’ll find in our full summary

Registered users get access to the Full Podcast Summary and Additional Materials. It’s easy and free!
Start your free trial today

The Unique Dynamics of Founder-Led Companies

Additional Materials

Counterarguments

  • Founders' personal connection to their company can sometimes lead to bias and a lack of objectivity, potentially hindering the company's growth or adaptation to new market conditions.
  • The authority to make large-scale changes can also result in founders making impulsive decisions that may not be in the best interest of the company or its stakeholders.
  • While founders may understand the intricacies of their company, this deep involvement can sometimes prevent them from seeing the bigger picture or embracing necessary changes that an external perspective might reveal.
  • Some founders are able to adapt and scale their leadership style with their growing comp ...

Actionables

  • You can deepen your connection to your projects by writing a "founder's diary" where you document your emotional journey, challenges, and triumphs, much like a parent would in a baby book. This practice can help you reflect on your passion and dedication, and serve as a motivational tool when facing tough decisions or considering significant changes to your project.
  • Develop a "change readiness checklist" to assess your willingness to implement major shifts in your projects or business ventures. This list should include criteria like understanding the risks, having a clear vision for the change, and being prepared to address stakeholders' concerns. By regularly reviewing this checklist, you can become more comfortable with making bold decisions, such as rebranding or restructuring.
  • Create a "future-proofing plan" for your initiatives by identif ...

Get access to the context and additional materials

So you can understand the full picture and form your own opinion.
Get access for free
CEO Diaries: Airbnb’s Founder Brian Chesky on Brutal Rejection, Great Leadership, and The Biggest Mistake Founders Make!

The Importance of Company Culture and Team-Building

Brian Chesky, CEO of Airbnb, stresses that company culture and team-building are vital to the success of any corporation, placing focus on daily behaviors and centralized leadership as the core of a thriving company environment.

Culture Is how a Company Operates, Shaped by Leaders' Lessons From Tough Experiences

Culture Is Reflected In Daily Behaviors and Decision-Making, Not Just Values

Chesky emphasizes that culture extends beyond a list of values and seeps into the daily behaviors and decision-making within a company. Describing culture as the shared way of doing something, Chesky notes that it often stems from tough times and is mirrored in the behavior of leaders which employees then follow.

Creating Culture: Leaders Shape and Reinforce Desired Behaviors

Chesky underscores that to genuinely build a company culture, it's not enough to talk about values. Leaders must actively shape and reinforce behaviors within their teams. He highlights that leaders design culture by example and need to constantly maintain and adjust it, similar to how a gardener tends to plants. In this light, setting an example for a culture of excellence means upholding high standards that embed themselves in the company's practices, even in the absence of its leaders.

A Healthy Company Culture Is Key to Success, as It Is the "Ultimate Intellectual Property" Bonding People, Resources, and Strategy

Chesky asserts that culture is the ultimate intellectual property of a company, acting as the binding agent for people, resources, and strategy. He defines a company as an entity made up of a group of ...

Here’s what you’ll find in our full summary

Registered users get access to the Full Podcast Summary and Additional Materials. It’s easy and free!
Start your free trial today

The Importance of Company Culture and Team-Building

Additional Materials

Clarifications

  • Culture within a company encompasses more than just stated values; it influences how employees behave and make decisions daily. This means that the culture of a company is not just about what is written on paper but is deeply ingrained in the actions and choices of individuals within the organization. Essentially, culture shapes the way things are done within a company, impacting the overall atmosphere and guiding how employees interact and work together. Leaders play a crucial role in setting the tone for this culture through their own behaviors and by actively reinforcing desired actions among their teams.
  • Leaders' lessons from tough experiences shape company culture by influencing their behavior, which is observed and emulated by employees. When leaders navigate challenges, their responses and decisions become a model for how to handle adversity within the organization. This behavior, when consistent and aligned with the company's values, helps establish a culture that reflects resilience, problem-solving skills, and adaptability.
  • A healthy company culture acts as a unique asset, shaping how individuals within the organization interact, make decisions, and work towards common goals. It goes beyond tangible assets like technology or products, as it influences employee behavior, collaboration, and overall performance. This intangible quality can be a significant competitive advantage, attracting and retaining talent, fostering innovation, and driving success. By nurturing a strong culture, a company can create a cohesive environment where people, resources, and strategic objectives align harmoniously.
  • Brian Chesky aims to maintain the energetic and collaborative atmosphere typically found in startups even as Airbnb expands its operations worldwide. This goal involves preserving the innovative and dynamic work environment that is often associated with smaller, more agile companies. By prioritizing this startup-like culture, Chesky hopes to encourage creativity, teamwork, and a sense of shared purpose among employees, regardless of the company's growth and global reach. This approach is intended to susta ...

Counterarguments

  • While company culture is important, it is not the only determinant of success; market conditions, product quality, and financial management also play critical roles.
  • Daily behaviors and decision-making are influenced by culture, but they can also be shaped by individual personalities, external pressures, and immediate business needs.
  • Leaders do influence culture, but it can also emerge organically from the bottom up, influenced by employees at all levels.
  • The idea that leaders alone can shape and reinforce culture may overlook the importance of employee participation and buy-in for a culture to be truly effective.
  • Intellectual property such as patents, trademarks, and trade secrets can also be critical to a company's success, not just culture.
  • While culture is important for cohesion, excessive focus on culture can lead to groupthink and stifle diversity of thought.
  • Maintaining startup energy and collaboration at scale can be challenging, and some level of bureau ...

Get access to the context and additional materials

So you can understand the full picture and form your own opinion.
Get access for free

Create Summaries for anything on the web

Download the Shortform Chrome extension for your browser

Shortform Extension CTA