IMO with Michelle Obama and Craig Robinson Be a Different Kind of Leader with Brian Chesky
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May 21, 2025 
Brian Chesky, Co-founder and CEO of Airbnb, shares insights on building connections and the evolution of tech's role in society. He reveals the quirky backstory of Airbnb's early success involving breakfast cereal. The conversation also dives into the challenges modern entrepreneurs face, particularly in navigating the tech landscape. Chesky offers surprising dating advice he received during the pandemic, emphasizing the importance of authentic connections and balancing digital interactions with real-life experiences.
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Airbnb's Origin Story
- Brian Chesky started Airbnb by renting out air mattresses for a design conference in 2007.
- They funded their startup by selling Obama-themed breakfast cereal when bookings dropped after the event.
Social Media's Connection Risk
- Social media risks replacing real-life connection with performance and following.
- This shift can worsen loneliness and societal division if not addressed.
Technology as a Tool
- Technology should be viewed as a tool, not inherently good or bad.
- Its impact depends on how people choose to use it and it requires intentional design.