Airbnb CEO Brian Chesky says the skills that helped him build the company were not enough to prepare him for running a global business, forcing him to rethink how he hired executives, managed employees and made strategic decisions as the startup expanded.
Speaking on Monday’s episode of the How I Built This podcast with host Guy Raz, Chesky described the transition from founder to chief executive as a difficult adjustment. While creating products and building a business came naturally to him, managing people and coordinating a growing organization required skills he had not developed to the same extent.
“I think I was pretty much naturally a great founder, and I was naturally a terrible CEO,” Chesky said.
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His experience offers a view into a challenge common among fast-growing companies: the capabilities required to establish a business are not always the same as those needed to manage it at scale. Founders often begin with direct control over product development, hiring and daily decisions. As organizations expand, they must delegate authority, establish management structures and ensure that different teams pursue a common direction.
For Chesky, the adjustment involved recognizing three mistakes that affected his early leadership: relying too heavily on experienced executives, avoiding difficult personnel decisions, and allowing too many competing priorities to shape the company’s direction.
1. Hiring Experienced Executives Without Staying Close Enough
Chesky said he initially followed advice that founders should recruit highly experienced executives and then give them room to run their departments.
He later concluded that this approach was not always appropriate for a young company. Rather than hiring executives whose experience came primarily from managing large organizations, he said startups need people who are slightly ahead of the founder in experience, possess strong capabilities, and remain closely involved in building the business.
“You’ve got to hire people just a little bit ahead of you that are smart, hungry, and you got to stay really close to them,” he said.
The problem, according to Chesky, was that he sometimes allowed the experience of senior executives to outweigh his own understanding of Airbnb’s business. When his instincts pointed in one direction and experienced managers recommended another, he usually deferred to them.
“The hard part for me was sometimes my intuition would tell me one thing, and they’d tell me another. And what do I do when my intuition and their experience collide? Usually I deferred, and that was usually a mistake,” he said.
He also found that executives recruited from larger companies could struggle to adapt their management approaches to a startup environment. Running an established corporation, where processes and organizational structures are already in place, is different from building systems and products in a company that is still developing its identity.
“They also come from companies where they didn’t build it. They managed it. And now they have to build it,” Chesky said.
The lesson is not that founders should avoid experienced executives. Rather, their expertise must match the company’s stage of development. A manager accustomed to operating within a mature organization may bring valuable knowledge but still struggle with the uncertainty, speed, and resource constraints of a startup.
Chesky’s account also highlights the importance of a founder retaining sufficient involvement in major decisions. Delegation can help a company scale, but excessive distance between the CEO and key operating teams can weaken the founder’s ability to identify problems early or challenge decisions that do not fit the company’s priorities.
2. Avoiding Difficult Conversations and Accountability
Chesky’s second mistake involved his reluctance to confront employees when their performance fell short.
He said he found it difficult to know when to give colleagues direct instructions and when to address problems with their work. His desire to maintain positive relationships sometimes prevented him from taking action when employees were not meeting expectations.
“I felt cautious about being a boss,” he said. “I think I was a little bit of a people pleaser. I wanted people to like me.”
He described himself as conflict-averse, saying that when an employee was not working out, he sometimes delayed making a decision.
In some cases, he took on employees’ responsibilities himself rather than addressing the underlying performance problem. Although this may have helped resolve immediate operational issues, it risked creating an unhealthy management pattern in which the CEO compensated for weaknesses elsewhere in the organization.
Such behavior can become difficult to sustain as a company grows. A chief executive who repeatedly takes over unfinished work may become a bottleneck, while employees receive insufficient feedback about their performance and responsibilities.
Chesky’s experience points to the difference between being supportive and avoiding accountability. Effective management requires employees to understand what is expected of them, receive direct feedback, and face consequences when performance does not improve.
For a founder leading a rapidly expanding company, difficult personnel decisions can also affect the wider organization. Retaining an employee who is not suited to a role may slow down teams, weaken execution, and create uncertainty about performance standards.
3. Failing to Establish Clear Priorities
Chesky’s third mistake was not saying “No” often enough. He said allowing executives to pursue competing priorities left the company without a sufficiently clear direction.
He compared the situation to passengers in a car who each want to travel to a different destination. Without a single agreed direction, the organization risks spending time and resources on initiatives that do not advance the same objective.
“The right way is one way. And one way has to be your way,” he said.
The consequences, he warned, can extend well beyond the tenure of the executive responsible for a particular decision.
If a senior manager takes a team down a path that the CEO does not support, the company may spend years correcting the consequences, even after that executive has left.
“They’ve gone down a path for two years. Guess what happens? They leave. You might spend five or 10 years fixing or correcting that decision that person made,” Chesky said.
This is a significant challenge for companies with multiple departments and increasingly complex operations. Executives naturally develop priorities based on their areas of responsibility, but those priorities can conflict with the broader needs of the business. The CEO must decide which initiatives deserve resources and which should be abandoned.
Airbnb’s challenge of maintaining focus has become more consequential as the company has grown beyond its original accommodation-booking model into a wider travel platform. Expansion creates opportunities, but it also increases the risk of spreading management attention and investment across too many initiatives.
Chesky’s comments offer a broader lesson about the changing responsibilities of company founders. The ability to identify an opportunity, build a product, and persuade people to support an idea can establish a successful business. Sustaining that business requires a different discipline: hiring people suited to the company’s stage, enforcing accountability, and maintaining a clear set of priorities.