Brian Chesky
Co-founder and CEO of Airbnb
Where to hear and read about Brian Chesky1 episode or test
Brian Chesky is co-founder and CEO of Airbnb, a trained industrial designer who rebuilt the company as a founder-led, functional organization after the pandemic cut 80% of its business in eight weeks. The most useful lesson is that a product-led founder should stay in the details and run one company on a single rolling roadmap, rather than delegating product to divisions.
Being in the details is what every responsible company's board does to the CEO.
Brian Chesky’s new playbook
Brian Chesky: the story and the lessons
1Brian Chesky's path from art to Airbnb
Chesky spent most of his early life as an artist. At five he copied Norman Rockwell paintings, and at eight or nine he took up architectural drawing. A public high school art teacher, Ms. Williams, gave his family the confidence to back art, and he won a national art competition and a scholarship to RISD.
His mother worried an artist would earn less than a social worker. He asked Santa for poorly designed toys so he could redesign them.
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Brian Chesky’s new playbook
Brian Chesky explains how he moved Airbnb from a divisional, delegated structure to a functional, founder-led one with a single rolling two-year roadmap, two launches a year and weekly CEO reviews. The result is a company of fewer than 7,000 people that ships cohesive product releases and has far fewer bad surprises after the pandemic wiped out 80% of the business in eight weeks.
Chesky spent most of his early life as an artist. At five he copied Norman Rockwell paintings, and at eight or nine he took up architectural drawing. A public high school art teacher, Ms. Williams, gave his family the confidence to back art, and he won a national art competition and a scholarship to RISD.
His mother worried an artist would earn less than a social worker. He asked Santa for poorly designed toys so he could redesign them.