Podcasts · This Week in Startups

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

· 1 h 18 min

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

0:00 1:18:04

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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:

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

00:03:44 When Jason and Justin realized people watch gaming

00:05:52 Mahalo, Halo 3, and betting a company on 3% of its traffic

00:10:21 CLA: Get started with CLA's CPAs, consultants, and wealth advisors now at https://www.claconnect.com/withyou

00:11:42 The "zombie startup" years and Google's rejection

00:17:06 Instinct: the AI agent built for venture capitalists

00:19:43 Sentry: New users can get $240 in free credits when they go to https://sentry.io/twist and use the code TWIST26

00:28:08 Kozmo.com and the era of "make number go up"

00:30:06 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

00:32:57 Why AI companies have to monetize faster

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

00:37:24 An early rejection of "founder mode"?

00:38:33 Brian Chesky on episode 1735 (May 2023)

00:39:27 "I hope that's not the only idea you're working on"

00:43:27 What 10% of Airbnb for $150K is worth today

00:46:05 Obama O's and the Y Combinator interview

00:48:15 Why investors fund unkillable, attention-hacking founders

00:54:37 Clip: Chesky on AI, deepfakes, and authenticity

00:58:13 Is AI costing jobs or just making them busier?

01:05:04 Did AI create "millions of startups"?

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Links in the notes 20

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