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The Airbnb Playbook: How to Become the CEO Your Startup Needs

Every Management Rule Brian Chesky Learned the Hard Way

Guillermo Flor's avatar
Guillermo Flor
Nov 13, 2026
∙ Paid

In 2020 Airbnb lost 80% of its business in a matter of weeks.

That crisis is what turned Brian Chesky into a real CEO, twelve years after he started the company.

  • Airbnb went public in December 2020 and was valued at more than $100B by the end of its first trading day

  • for most of the decade before, Chesky doubted he would ever be a great CEO

  • the way he rebuilt his job inspired Paul Graham's essay on founder mode

  • his entire executive team eventually left

Chesky co-founded Airbnb in 2008 as a designer with no management experience. For years he followed the standard advice: hire experienced people, trust them and get out of their way. He now calls that advice a death sentence for a young company.

So he rebuilt the job around a few rules: who to hire, when to say no, how deep to go into the details and how to get people to disagree with him.

→ He still runs about 20 projects at a time, each on its own review rhythm.

📚 In this newsletter, I break down the management rules Airbnb's founder learned the hard way, with clips from his interview with Guy Raz on How I Built This and the takeaways for founders.

Refer a friend

Inside you will find:

  1. How to Hire and Fire Before You Have an HR Team
    See who Chesky hires for a young company, why he regrets deferring to senior hires and the test he uses to read people.

  2. How to Keep the Whole Company Moving in One Direction
    Find out how Airbnb ended up doing everything at once and the three things Chesky swore he'd never do.

  3. How to Stay in Every Detail Without Slowing the Team Down
    Learn how he runs reviews with the whole chain of command in the room and why he overrules his team only 10% of the time.

  4. How to Never Have to Kill a Six-Month Project
    See the kickoff checklist and the daily, weekly and monthly rhythms he uses across 20 projects.

  5. How to Get Your Team to Tell You You're Wrong
    Find out how a tagline he was sure about taught him to take the opposite side of his own ideas.


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