World Model · podcast knowledge graph

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

2026-10-01 · 78 min · 46 entities

episode page audio

Asserted relationships

  • → references twistartups.substack.com website
    0.77
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://twistartups.substack.com/
  • → references Airbnb company
    0.77
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://en.wikipedia.org/wiki/Airbnb
  • → references airbnb.com place
    0.77
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://airbnb.com/
  • → references thisweekinvc.substack.com website
    0.77
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://thisweekinvc.substack.com/
  • → references Halo 3 concept
    0.77
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://en.wikipedia.org/wiki/Halo_3
  • → references Weblogs, Inc company
    0.77
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://en.wikipedia.org/wiki/Weblogs,_Inc.
  • → hosted by Jason Calacanis person
    0.55
    evidence rules-v5
    Feed author/publisher: Jason Calacanis
  • → founded Justin.TV company
    0.54
    evidence rules-v5
    co-founder of Justin.tv
  • → works at Justin.TV company
    0.50
    evidence rules-v5
    co-founder of Justin.tv
  • → discusses Technology company
    0.40
    evidence rules-v5
    Feed category: Technology
  • → references ThisWeekIn website
    0.38
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://youtube.com/thisweekin
  • → references Twist website
    0.38
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": http://plaud.ai/twist
  • → references @Thisweekinstartups website
    0.38
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://tiktok.com/@thisweekinstartups
  • → references stripe.com website
    0.38
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://stripe.com/
  • → references lovable.dev person
    0.38
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://lovable.dev/
  • → references ycombinator.com website
    0.38
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://ycombinator.com/
  • → references Tech website
    0.38
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://claconnect.com/tech
  • → references partners.launch.co company
    0.38
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://partners.launch.co/
  • → references thisweekinai.ai website
    0.38
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://thisweekinai.ai/
  • → references twitch.tv website
    0.38
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://twitch.tv/
  • → references lightfield.app website
    0.38
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://lightfield.app/
  • → references Withyou website
    0.38
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://claconnect.com/withyou
  • → references instinct.co website
    0.38
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://instinct.co/

Entities found in this episode

websites 26

  • mentioned twistartups.substack.com website
    0.90
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://twistartups.substack.com/
  • mentioned thisweekinvc.substack.com website
    0.90
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://thisweekinvc.substack.com/
  • references twistartups.substack.com website
    0.77
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://twistartups.substack.com/
  • references thisweekinvc.substack.com website
    0.77
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://thisweekinvc.substack.com/
  • mentioned ThisWeekIn website
    0.45
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://youtube.com/thisweekin
  • mentioned Twist website
    0.45
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": http://plaud.ai/twist
  • mentioned @Thisweekinstartups website
    0.45
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://tiktok.com/@thisweekinstartups
  • mentioned stripe.com website
    0.45
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://stripe.com/
  • mentioned ycombinator.com website
    0.45
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://ycombinator.com/
  • mentioned Tech website
    0.45
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://claconnect.com/tech
  • mentioned thisweekinai.ai website
    0.45
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://thisweekinai.ai/
  • mentioned twitch.tv website
    0.45
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://twitch.tv/
  • mentioned lightfield.app website
    0.45
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://lightfield.app/
  • mentioned Withyou website
    0.45
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://claconnect.com/withyou
  • mentioned instinct.co website
    0.45
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://instinct.co/
  • references ThisWeekIn website
    0.38
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://youtube.com/thisweekin
  • references Twist website
    0.38
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": http://plaud.ai/twist
  • references @Thisweekinstartups website
    0.38
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://tiktok.com/@thisweekinstartups
  • references stripe.com website
    0.38
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://stripe.com/
  • references ycombinator.com website
    0.38
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://ycombinator.com/
  • references Tech website
    0.38
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://claconnect.com/tech
  • references thisweekinai.ai website
    0.38
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://thisweekinai.ai/
  • references twitch.tv website
    0.38
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://twitch.tv/
  • references lightfield.app website
    0.38
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://lightfield.app/
  • references Withyou website
    0.38
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://claconnect.com/withyou
  • references instinct.co website
    0.38
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://instinct.co/

companys 11

  • mentioned Airbnb company
    0.90
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://en.wikipedia.org/wiki/Airbnb
  • mentioned Weblogs, Inc company
    0.90
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://en.wikipedia.org/wiki/Weblogs,_Inc.
  • references Airbnb company
    0.77
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://en.wikipedia.org/wiki/Airbnb
  • references Weblogs, Inc company
    0.77
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://en.wikipedia.org/wiki/Weblogs,_Inc.
  • mentioned Justin.TV company
    0.68
    evidence rules-v5
    co-founder of Justin.tv
  • founded Justin.TV company
    0.54
    evidence rules-v5
    co-founder of Justin.tv
  • mentioned Technology company
    0.50
    evidence rules-v5
    Feed category: Technology
  • works at Justin.TV company
    0.50
    evidence rules-v5
    co-founder of Justin.tv
  • mentioned partners.launch.co company
    0.45
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://partners.launch.co/
  • discusses Technology company
    0.40
    evidence rules-v5
    Feed category: Technology
  • references partners.launch.co company
    0.38
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://partners.launch.co/

persons 4

  • mentioned Jason Calacanis person
    0.70
    evidence rules-v5
    Feed author/publisher: Jason Calacanis
  • hosted by Jason Calacanis person
    0.55
    evidence rules-v5
    Feed author/publisher: Jason Calacanis
  • mentioned lovable.dev person
    0.45
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://lovable.dev/
  • references lovable.dev person
    0.38
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://lovable.dev/

concepts 3

  • mentioned Halo 3 concept
    0.90
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://en.wikipedia.org/wiki/Halo_3
  • references Halo 3 concept
    0.77
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://en.wikipedia.org/wiki/Halo_3
  • 0.42
    evidence rules-v5
    Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344

places 2

  • mentioned airbnb.com place
    0.90
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://airbnb.com/
  • references airbnb.com place
    0.77
    evidence rules-v5
    Link in episode "Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344": https://airbnb.com/
Episode description as stored
This Week In Startups is made possible by: Plaud: http://Plaud.ai/twist CLA: https://claconnect.com/tech Sentry: http://sentry.io/twist Lightfield: http://sentry.io/twist 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://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 TWIST26 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"? Subscribe to our newsletters on Substack: TWiST: https://twistartups.substack.com/ TWiAI: https://www.thisweekinai.ai/ TWiVC: https://thisweekinvc.substack.com/ Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp Follow Lon: X: https://x.com/lons Follow Jason: X: https://twitter.com/Jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis Check out all our partner offers: https://partners.launch.co/ Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Sloot