Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344
September 30, 2026 · 1 h 18 min
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Show notes
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Today’s show:
Google once interviewed the entire Justin.tv (now Twitch) team and then walked away from an acquisition deal, saying they weren’t good enough. Seven investors passed on buying 10% of Airbnb for $150,000, a stake pegged at roughly $9.25 billion today.
Lon Harris and Alex Wilhelm revisit classic TWiST interviews with Justin Kan of Twitch and Brian Chesky of Airbnb to find out what those founders understood that the market didn't.
PLUS, how did a box of cereal win over Paul Graham and get Airbnb into Y Combinator?
Flashback Guests:
Justin Kan on X: https://x.com/justinkan Twitch: https://www.twitch.tv/
Justin Kan (@justinkan) on X
Brian Chesky on X: https://x.com/bchesky AirBnB: https://www.airbnb.com/
Relevant Links:
TWiST E900: Justin Kan, co-founder of Justin.tv, Twitch & Atrium (Feb 5, 2019) → https://thisweekinstartups.com/episodes/L3DP8VCE12s
TWiST E1735: Airbnb CEO Brian Chesky on early rejection, customer focus & AI (May 4, 2023) → https://www.youtube.com/watch?v=aZ-BjJZxNoA
Halo 3: the game that flooded Mahalo with traffic → https://en.wikipedia.org/wiki/Halo_3
Weblogs, Inc.: Jason's blog network, home of Engadget → https://en.wikipedia.org/wiki/Weblogs,_Inc.
Instinct: the invite-only personal AI agent from founder Noah Shinn → https://www.instinct.co/
AMD to acquire World Labs for $8.2B in stock; Li becomes AMD chief scientist (Bloomberg) → https://www.bloomberg.com/news/articles/2026-09-28/amd-to-buy-fei-fei-li-s-world-labs-ai-startup-for-8-2-billion
Lovable: where Lon says he'd rebuild a bad app in two hours → https://lovable.dev/
Y Combinator → https://www.ycombinator.com/
Paul Graham on X → https://x.com/paulg
Obama O's and Cap'n McCain's: the cereal that funded Airbnb → https://en.wikipedia.org/wiki/Airbnb#History
Stripe: what Paul Graham suggested they build instead → https://stripe.com/
Timestamps:
Justin Kan on episode 900 (Feb 2019)
When Jason and Justin realized people watch gaming
Mahalo, Halo 3, and betting a company on 3% of its traffic
CLA: Get started with CLA's CPAs, consultants, and wealth advisors now at https://claconnect.com/tech at https://www.claconnect.com/withyou
The "zombie startup" years and Google's rejection
Instinct: the AI agent built for venture capitalists
Sentry: New users can get $240 in free credits when they go to https://sentry.io/twist and use the code TWIST
Kozmo.com and the era of "make n