Design Matters with Debbie Millman Brian Chesky
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Jan 26, 2026 
Brian Chesky, co-founder and CEO of Airbnb and trained industrial designer, talks about how imagination and design shaped his path from art school to building a worldwide hospitality community. He recalls redesigning toys and cities, RISD rituals like 200 self-portraits, founding Airbed & Breakfast, solving trust for adoption, and how AI and philanthropy factor into design-led leadership.
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Art School Reframes Design As Power
- RISD's community of misfits turned into an ambition engine that reframed design as world-building, not ornamentation.
- Realizing designers can change systems altered Chesky's sense of agency and career possibility.
Learn Entrepreneurship By Running Clubs
- Run self-directed projects to learn entrepreneurship: create vision, mobilize people, and sell them on it.
- Treat volunteer clubs as practice for budgets, marketing, and leadership.
Commencement Moonwalk Moment
- Brian prepared an over-the-top, satirical RISD commencement speech and performed it in a white tuxedo to a crowd of 6,000.
- The stunt taught him public performance and confirmed he enjoyed speaking on big stages.