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This Week in Startups · October 1, 2026 · 1h 18m

Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344

Brian Chesky, Justin Kan

Lon Harris and Alex Wilhelm revisit classic TWiST interviews with Justin Kan and Brian Chesky, exploring the early rejections that shaped Twitch and Airbnb. Google walked away from an acquisition deal with Justin.tv, saying the team wasn't good enough, while seven investors passed on buying 10% of Airbnb for $150,000—now worth roughly $9.25 billion. The discussion covers how both founders persevered, and the unconventional cereal-box hustle that helped Airbnb get into Y Combinator.

This summary was generated from show notes and public descriptions, not from a full transcript review. Details may contain inaccuracies.

Preview

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Google's Rejection That Built Twitch11:42
Google interviewed the entire Justin.tv team for an acquisition but walked away, saying they weren't good enough—only for the company to later become Twitch, a multi-billion-dollar platform.
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The $9.25 Billion Missed Investment in Airbnb43:27
Seven investors passed on buying 10% of Airbnb for $150,000; today, that stake would be worth approximately $9.25 billion.
ClaudeChatGPTGemini

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