Squawk Pod Leaders Playbook: Inside Airbnb 1/28/26
Jan 28, 2026
Brian Chesky, co-founder and CEO of Airbnb who scaled the home-sharing platform and steered it through major crises. He recalls the airbed origin, joining Y Combinator, and finding product-market fit during a downturn. He explains decisive crisis moves, leading through COVID with cash and reorgs, founder-mode involvement to speed decisions, and how a designer mindset shapes product-led scaling.
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Airbed Origins Sparked Airbnb
- Brian Chesky and Joe Gebbia rented out air mattresses during a sold-out conference to cover rent and launched Air Bed and Breakfast.
- The guests arrived as strangers and left as friends, revealing the broader idea of trusted home sharing.
Crisis Forced A Trust Guarantee
- In 2011 a host's apartment was trashed and public outrage threatened Airbnb's survival.
- Chesky apologized, created a retroactive $50,000 guarantee, and turned a weakness into a trust-building strength.
Choose Principled Decisions Under Uncertainty
- When outcomes are uncertain, make a principal decision based on how you want to be remembered.
- Use defining, values-driven choices to guide action when you cannot game-theory every scenario.