Siri cofounder's $100 VC stunt: let investors lose to AI in a live demo
Scobleizer · x · 2026-09-16
- At a Google conference, Scobleizer heard Siri cofounder Adam Cheyer recount a classic 2009 fundraising tactic.
- Cofounder Dag Kittlaus would arrive early, place a $100 bill on the table, and challenge VCs to book a highly rated Indian restaurant near his hotel in minutes. With OpenTable, Yelp, and Google Maps all siloed, they couldn't do it.
- He then asked Siri to do it in one sentence — and it worked. Siri was arguably the first consumer AI app; Cheyer had run the world's largest AI team at SRI International.
Related event: Siri Co-founder's $100 Pitch Trick That Won Over VCs(2 posts)→
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