Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344
This Week in StartupsShow 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:
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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This Week In Startups is made possible by:
This Week In Startups is made possible by: Plaud: https://plaud.ai/twist Northwest Registered Agent: https://www.northwestregisteredagent.com/twistdomain Vanta: https://www.vanta.com/twist Rippling: https://rippling.ai/twist Today’s show: Jason can’t stop praising Nathan Fielder’s new A24 hybrid documentary about Elizabeth Holmes and Theranos, “You Can See Everything,” and he’s insisting that Lon check it out before the next podcast. Hear his spoiler-free review, how the film upended his expectations based on Fielder’s previous work, and why Lon also recommends Lance Oppenheim’s HBO Max series “Ren Faire.” Plus, we’re talking to Clone Robotics co-founder and CEO Dhanush Radhakrishnan about why he thinks robots should not just be humanoid but should look and move precisely like humans. We’re digging deep into how his hydraulic myofiber artificial muscle technology alters and even improves on the pulley-based systems being deployed by competitors, why he thinks the models that power domestic helper-bots will be commoditized, and how quickly he thinks he can put a robo-butler in every American home. Plus we’re comparing the potential impact of Anthropic’s new Public Benefit Fund vs. Elon Musk’s plan to give every baby a share of SpaceX, and re-considering simulation theory after Odyssey dropped an artificial fruit fly brain into an artificial landscape. Guest Dhanush Radhakrishnan on X: https://x.com/dhanushisrad Clone Robotics: https://clonerobotics.com/ Related Links “You Can See Everything” trailer: https://www.youtube.com/watch?v=HvW_N5p1q44 “You Can See Everything” on Rotten Tomatoes: https://www.rottentomatoes.com/m/you_can_see_everything John Carreyrou’s Theranos investigation (Wall Street Journal): https://www.wsj.com/articles/theranos-has-struggled-with-blood-tests-1444881901 “Ren Faire” HBO Max trailer: https://www.youtube.com/watch?v=CHZUVTrrexE “Nathan for You”: Smokers Allowed clip (Comedy Central): https://www.youtube.com/watch?v=HttB2fYAm-8 Anthropic: Investing in the Public Benefit: https://www.anthropic.com/news/public-benefit-fund Elon Musk SpaceX pledge: https://x.com/elonmusk/status/2112089556615123114 Dell’s $6.25B Invest America commitment: https://www.onedell.com/investamerica/ Odyssey Fly Simulation X post: https://x.com/odysseyml/status/2111589148146749616 Chris Williamson: “The ElevenLabs Situation is Crazy”: https://www.youtube.com/watch?v=lxDNHLgWInU ElevenLabs’ Legendary Voices marketplace: https://elevenlabs.io/iconic-marketplace TWiST newsletter on Substack: https://twistartups.substack.com/ LAUNCH Careers page: https://careers.launch.co/ Timestamps: 00:00 Intro 00:10 Plaud - If your work depends on conversations - interviews, meetings, calls - you need a Plaud NotePin S. You can check it out at https://plaud.ai/twist and use code TWIST for 10% off! 03:18 Jason's "You Can See Everything" reaction 14:37 Northwest Registered Agent - Got a new business idea? Northwest Registered Agent helps you bring it to life. Get a free domain, email, phone number, and more - with no purchase required! Learn more at https://www.northwestregisteredagent.com/twistdomain 15:27 What films max out RT's critic and audience scores 20:08 Anthropic commits 5% equity to Public Benefit Fund 24:28 Would equity change how Americans feel about AI? 27:08 Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist 38:38 Rippling - Thanks to our partners at Rippling! Head to https://rippling.ai/twist and get the only AI built to give you full visibility across your startup and take complex actions across your entire business. 39:48 Dhanush from Clone Robotics joins the show 42:43 How hydraulic muscle technology actually works 54:55 When can we have our robot butlers please? 56:55 Where will Clone get its robot brains? 1:12:17 Odyssey trapped a fake fly brain in a simulated environment 1:23:09 Did ElevenLabs steal a podcaster's voice? 1:30:13 Check us out on Substack! Subscribe to our newsletters on Substack: TWiST: https://twist
This Week In Startups is made possible by:
This Week In Startups is made possible by:
This Week In Startups is made possible by: