Airbnb CEO Brian Chesky on Why Founders Must Learn to Lead Differently
Airbnb’s scale makes Brian Chesky’s distinction between founding a company and running one especially relevant. The CEO, who has led Airbnb since its 2007 launch, said on the How I Built This podcast that he was “naturally a great founder” but “naturally a terrible CEO.” The contrast is blunt, and it points to a problem that can be obscured by a founder’s early success: the person who sees an opportunity and gets a company started may need to learn a different set of habits to lead it as it grows. Chesky’s description is his own assessment, but the distinction is useful beyond Airbnb.
Airbnb now has more than 5.5 million hosts and reported $12.24 billion in revenue in 2025, according to Stock Analysis. Those figures show the scale of the business Chesky is discussing, but they don’t explain how it was built or establish that any single leadership approach caused its growth. His account instead points to a challenge that can outlast a company’s early expansion: the abilities that help a founder create a business don’t necessarily prepare that person to manage a larger organization. The transition can be uncomfortable precisely because the founder’s first instincts may have been rewarded for years.
Building a company and leading it require different skills
Chesky described founding as a practice that can begin long before a person starts a business. He said he had about 20 years of experience making and taking apart things, including Christmas toys, by the time he launched Airbnb at age 26. That history gave him a foundation for creating a company, but it didn’t teach him how to lead one. Making something work through experimentation is a different task from setting direction for employees, deciding who should own which decisions, and helping a group work toward the same goal.
For a young business, he argued, the familiar advice to hire accomplished people, trust them and leave them alone can backfire. “That is what you do once you are very mature,” he said. “That is a death sentence to a young company.” His point is about timing: practices that make sense in a settled organization may not fit a company whose roles, priorities and ways of working are still taking shape. A new hire can bring experience and skill, but those qualities don’t automatically supply the context needed to make decisions in an organization that hasn’t yet established how it operates.
His alternative is to hire people who are smart and hungry, with skills slightly ahead of the company’s current needs, and then stay closely involved in their work. That approach asks the CEO to do more than recruit capable staff. It also makes the CEO responsible for explaining what matters now, giving people enough direction to act, and adjusting expectations as the company develops. Close involvement can help teams build shared understanding, though it also puts more weight on the leader’s judgment about when guidance is useful and when it starts to limit others’ work.
Leadership means acting on judgment
Chesky said he was initially cautious about giving direction, particularly to employees who seemed older or more experienced. He wanted people to like him, he said, and sometimes deferred to their judgment even when his own instincts pointed elsewhere. In retrospect, he saw that hesitation as a mistake. The admission is more revealing than a simple call for stronger executive authority: it describes how the desire to maintain good relationships can leave a leader avoiding a decision that the role requires.
That doesn’t mean employees are wrong when they disagree with a CEO, Chesky said. It does mean the CEO has to raise the disagreement and examine it rather than automatically yielding to experience or avoiding an uncomfortable conversation. A leader who challenges advice still has to listen to it; otherwise, “having a point of view” can become a cover for dismissing useful dissent. The harder task is to make the disagreement explicit, understand what each person is basing their view on, and then take responsibility for the decision.
He also described building a culture where employees make sound decisions without the CEO present as one of the hardest parts of the job. By comparison, he said, profitability and expense management are easier problems to address. The distinction helps explain why leadership can’t be reduced to a list of operational targets: a company needs people to use judgment across situations the CEO can’t personally supervise. That takes time and depends on whether employees understand the organization’s priorities, have clear responsibility, and can raise concerns when a decision is uncertain. There’s no shortcut.
Chesky’s account suggests that early-stage leadership calls for more direct involvement than many standard management slogans imply. As a company matures, its leaders may be able to give teams greater autonomy; before then, hiring judgment, clear direction and the CEO’s willingness to challenge advice can shape whether the organization develops effectively. The balance is difficult: too little guidance can leave employees guessing, while too much can keep every decision tied to the founder. The point isn’t that one level of involvement fits every company, but that leaders have to notice when the company’s needs have changed.
What the transition means as a company grows
Airbnb’s scale makes the distinction between founder and CEO more than a matter of personal development. At a business with millions of hosts, the decisions and working habits established inside the organization can matter across a much wider network of people. That doesn’t show that Chesky’s approach is the only way to lead a growing company, or that every founder should manage in the same manner. It does make his account a useful reminder that growth can change the job before a leader has fully changed with it.
Here’s the thing: a founder’s early strengths can become a poor guide to what the company needs next. The instinct to stay close to the work may help clarify priorities when teams are still forming, but a leader also has to build conditions in which employees can make decisions independently. (And this is the part most people overlook.) Delegation isn’t simply stepping away; it depends on the clarity and judgment the organization has built while the CEO was involved.
This is more significant than it looks. If you’re working in this space, the practical question raised by Chesky’s comments is how a leader can tell whether close involvement is giving a team direction or keeping it dependent. His answer, as described in the interview, puts weight on hiring, guidance and candid disagreement. The longer-term test is whether employees can carry the company’s priorities into decisions the CEO won’t see in advance. That’s the work of building a culture, not just managing a calendar.