Siri cofounder's $100 VC demo trick: booking dinner before it was possible

Scobleizer · x · 2026-09-16

Scoble recounts a pitch story from Siri cofounder Adam Cheyer: in 2009, Dag Kittlaus would put $100 on the table at VC meetings and challenge anyone to book a well-rated Indian restaurant on an iPhone in minutes — impossible when OpenTable, Yelp, and Google Maps didn't integrate. Then one "Hey Siri" demo won the room. Cheyer ran SRI's AI team, then the world's largest; Siri was arguably the first consumer AI app.

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