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

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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:

0:00 Justin Kan on episode 900 (Feb 2019)

3:44 When Jason and Justin realized people watch gaming

5:52 Mahalo, Halo 3, and betting a company on 3% of its traffic

10:21 CLA: Get started with CLA's CPAs, consultants, and wealth advisors now at https://claconnect.com/tech at https://www.claconnect.com/withyou

11:42 The "zombie startup" years and Google's rejection

17:06 Instinct: the AI agent built for venture capitalists

19:43 Sentry: New users can get $240 in free credits when they go to https://sentry.io/twist and use the code TWIST

28:08 Kozmo.com and the era of "make number go up"

30:06 Lightfield: Name one person who's ever enjoyed updating a CRM. Exactly. Lightfield's AI agent does it for you - it even prospects and books your meetings. Used by thousands of startups. Free at https://lightfield.app/

32:57 Why AI companies have to monetize faster

34:00 Clip: Justin Kan on knowing yourself as a founder

37:24 An early rejection of "founder mode"?

38:33 Brian Chesky on episode 1735 (May 2023)

39:27 "I hope that's not the only idea you're working on"

43:27 What 10% of Airbnb for $150K is worth today

46:05 Obama O's and the Y Combinator interview

48:15 Why investors fund unkillable, attention-hacking founders

54:37 Clip: Chesky on AI, deepfakes, and authenticity

58:13 Is AI costing jobs or just making them busier?

1:05:04 Did AI create "millions of startups"?

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