The founder mistake Airbnb’s CEO thinks kills great companies

This article summarizes an episode of Invest Like The Best’s video series  featuring Brian Chesky, CEO of Airbnb.

Brian Chesky, CEO of Airbnb / Photo credit: Airbnb

Brian Chesky, the CEO of Airbnb, believes the transition from startup founder to corporate manager is extremely difficult. Building a company relies on instinct, while running a large business requires systems and operational discipline.

That realization pushed him to take back control and rebuild how Airbnb managed products.

The dangers of hiring bosses

As companies grow, founders are often encouraged to hire managers and step away. Chesky argues that blindly following this advice creates a disconnect between a founder’s vision and daily operations.

“No one is born a good CEO,” he shares. “The job of a CEO is completely counterintuitive, and almost all of your intuition about what to do is wrong.”

He warns that avoiding operational involvement creates long-term problems. “You hire somebody, they build an empire, they leave, and now you have to unwind their empire—and it takes, like, four years.”

Stepping back separates leaders from the product
This disconnect is often fueled by modern tech culture, which falsely praises giving away power rather than actually managing the business.

He says, “Founders were overdelegating their companies to these professional managers; they were detaching themselves, and they were being managed rather than managing the company.”

Taking back control

Re-engaging with the business means resisting workplace cultures that push leaders to become hands-off cheerleaders. Fear of being labeled “micromanagers” often keeps managers away from details, leaving teams from the main goal.

“Control and power are not zero-sum,” Chesky notes. “If I have power, I can therefore give you power… It’s about the idea that the car has a steering wheel. You turn it left, and it actually goes left.”

He argues that leaders should deeply understand the work before delegating it. He advises founders to start with tight control, monitor performance closely, and only grant freedom slowly as workers prove their skills.

How AI changes work

Taking back hands-on control is becoming a survival skill, as the rise of AI threatens to flatten company structures by automating the work of middle managers. This shift in how companies operate is driven by a few realities:

• Information scarcity used to require deep layers of middle management.
• Software makes massive cross-functional collaboration practically free.
• Pure people managers will lose their jobs.
• The future belongs exclusively to highly skilled individual contributors (ICs).

The lack of tools for regular people

The trap of growing too fast

Hiring saves time

The mind behind high standards