This Week in Startups

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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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Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland

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Today’s show:

A product that would have cost $500,000 to build in 2006 now costs less than a used car. Jason put up $5,000 on an idea he'd been sitting on for 20 years, and so far, we’ve received dozens of amazing submissions from vibecode experts.
See how well the Top 3 demos fare, and which app was so good, Jason’s already thinking about spinning it off into a startup.
PLUS, an unhoused founder calls in asking how to raise money for not one but two pre-revenue startups? Hear Jason and Lon’s advice.

Submissions:

Submission 1 — https://annotated.wtf By Robert
Submission 2 — https://annotated.bytetalk.ai/feed By Alan Shiflett
Alan on X: https://x.com/alanshiflett
Submission 3 — https://anotated.com/ By Chirag Asarpota
Chirag on X: https://x.com/ChiragAsarpota

Relevant Links:

annotated.com bounty brief — https://annotated.lovable.app/
All active TWiST bounties — https://www.thisweekinstartups.com/bo...
The other open $5,000 bounty: a sidebar companion app for podcasts — https://www.notion.so/launch1/5K-Boun...

Timestamps:

0:00 Why Jason bought annotated.com
0:33 The original idea: highlight any sentence on the web and dispute it
1:25 The rules: the code is open source, and Jason can cancel any time
2:06 Submission 1: Robert's annotated.wtf
9:31 Every.io - For all of your incorporation, banking, payroll, benefits, accounting, taxes or other back-office administration needs, visit https://every.io11:36 Submission 1 Scoring
11:51 Submission 2: Allan Shifflet's take
13:19 What it got right: profiles, follower counts, trending topics
16:03 Submission 3: annotaed.com, and buying the typo domain on purpose
19:43 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....22:49 Final scores, and how to enter round two
24:11 Incubating annotated inside a venture firm
29:09 Sentry - New users can get $240 in free credits when they go to https://sentry.io/twist and use the code TWIST
29:41 Ask Jason: a homeless founder with two startup ideas

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Today’s show:

Timestamps:

0:00 Will Ternus take "massively big swings"?

3:43 Round 1: ElevenLabs

4:46 Round 1: Disney

6:18 Round 2: Sony

8:22 Round 2: Boston Dynamics

9:23 Round 3: Perplexity

10:02 AD: PayPal is built for all business. Get started at https://paypal.com/business

11:52 Round 3: DigitalOcean

13:02 More picks: Etched

14:30 More picks: Lucid

15:58 More picks: Superhuman

16:48 More picks: Higgsfield and more

18:09 Fans make their selections

19:47 AD: Got a new business idea? @northwestagent helps you bring it to life. Get a free domain, email, phone number, and more, with no purchase required! Learn more at www.northwestregisteredagent.com/twistdomain

25:37 Stacy Salvi of The90 joins

29:28 AD: Thanks to our partner, Odoo, the all-in-one business platform. Your first app is free! Get started today at https://Odoo.com/twist

34:38 How the app calculates your Sunscore

42:12 Building a UV research dataset

45:09 Should The90 make a version for men?

Names & Links

Stacy Salvi - https://www.instagram.com/stacysalvi/

The90 - https://the90.com/

Description

Wall Street suspects new Apple CEO John Ternus may do something predecessor Tim Cook almost never did: writing a huge check.

So Jason and Lon are playing “fantasy draft” with Apple’s balance sheet, choosing five real companies to acquire over five “rounds.” Disney buys them a ton of IP and unlocks theme park synergies. Sony gets them a gaming console and massive anime distribution. Boston Dynamics buys them lots of robots, while Etched nets them cheaper inference. So many options!

Then, we chat with Stacy Salvi of The90. Her wearable pendant tells you exactly how much sun damage you’re accumulating, long before you start to burn.

Guest

The90: https://the90.com/

Stacy Salvi on LinkedIn: https://www.linkedin.com/in/stacysalvi/

Relevant Links

John Ternus becomes Apple CEO: https://www.apple.com/newsroom/2026/04/tim-cook-to-become-apple-executive-chairman-john-ternus-to-become-apple-ceo/

Analyst: Ternus could bring bigger acquisitions: https://9to5mac.com/?p=1065466

“Grok Has Money” meme origin: https://x.com/gmfarcaster/status/2026318035103965414

Sunlight linked with lower COVID-19 deaths: https://www.ed.ac.uk/news/2021/sunlight-linked-with-lower-covid-19-deaths

Reid Hoffman: “If there aren’t any typos in this essay, we launched too late”: https://www.linkedin.com/pulse/arent-any-typos-essay-we-launched-too-late-reid-hoffman/

Draft Picks

ElevenLabs: https://elevenlabs.io/

Disney: https://thewaltdisneycompany.com/

Sony Group: https://www.sony.com/en/

Crunchyroll: https://www.crunchyroll.com/

Boston Dynamics: https://bostondynamics.com/

Perplexity: https://www.perplexity.ai/

DigitalOcean: https://www.digitalocean.com/

Etched: https://www.etched.com/

Rivian: https://rivian.com/

Lucid Motors: https://lucidmotors.com/

Superhuman: https://superhuman.com/

World Labs: https://www.worldlabs.ai/

PrismML: https://prismml.com/

Liquid AI: https://www.liquid.ai/

Kagi: https://kagi.com/

Sonos: https://www.sonos.com/en-us/shop

Whoop: https://www.whoop.com/

Oura: https://ouraring.com/

Peloton: https://www.onepeloton.com/

Subscribe to our newsletters on Substack:

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Follow Lon:

X: https://x.com/lons

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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 Slootman, Billy McFarland

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Today’s show:

An OpenAI agent breached Australia's Medicare statistics portal in June, and it took 84 days for the Frontier Lab to publicly acknowledge it. Jason and Lon dig into whether this is an important cautionary tale about alignment, or if PM Anthony Albanese looking to join the AI conversation.

Then Bryant Chou of Ploy joins to explain skipping pre-seed and seed entirely to raise $27M, and why he’s taking his time to build his all-in-one agentic solution for running businesses.

Learn why Google is launching four TPUs into orbit for Project Suncatcher. PLUS, how many robots a week is Tesla now shipping with Optimus, and Jensen Huang told Ezra Klein basic math no longer matters. Is he right? Can we forget long division, at last?

Guests:

Bryant Chou on X: https://x.com/bryantchou PloyAI: https://ploy.ai/

Relevant Links:

Ploy raises $27M seed led by First Round Capital and Y Combinator (Founderland) → https://www.founderland.ai/articles/webflow-co-founder-launches-ai-marketing-platform-with-27m-s-mqj8o952

OpenAI's $2M-in-tokens offer to every YC startup(TechCrunch via Yahoo) → https://finance.yahoo.com/sectors/technology/articles/sam-altman-makes-mic-drop-212302858.html

Original Bloomberg report on the a16z probe → https://www.bloomberg.com/news/articles/2026-08-17/andreessen-horowitz-focus-of-doj-probe-over-board-directors

Google: Project Suncatcher's first test launch on SpaceX's Transporter-18 → https://blog.google/innovation-and-ai/models-and-research/google-research/google-project-suncatcher-facts/

ABC News (Australia): full timeline, from the June 18 breach to OpenAI's Sept. 10 email → https://www.abc.net.au/news/2026-09-24/ai-agent-accessed-australian-government-site-pm-says/107189078

Ando emerges from stealth with $20M to take on Slack (TechCrunch) → https://techcrunch.com/2026/09/24/ando-eyes-slack-as-it-builds-team-messaging-platform-for-humans-and-agents-to-work-together/

Google's $900M investment in SpaceX's $1B round, January 2015 (VentureBeat) → https://venturebeat.com/technology/google-confirms-it-put-900m-into-spacexs-1b-round

Tesla ramps Optimus to several hundred robots a week; hands are the bottleneck (Electrek, summarizing The Information) → https://electrek.co/2026/09/25/tesla-optimus-production-ramp-hands-ai-generalization-problems/

Jensen Huang tells Ezra Klein forgetting basic math may not matter, and that he doesn't know his own address (Kotaku) → https://kotaku.com/nvidia-ceo-doesnt-care-that-kids-are-forgetting-basic-math-because-of-ai-i-actually-dont-know-my-address-2000737092

Sydney Sweeney's Novig "Just Sports" ad and the athlete backlash, including Amy Hunt's comment (Yahoo) → https://www.yahoo.com/entertainment/celebrity/articles/sydney-sweeney-novig-ad-controversy-172900515.html

Nike exits the S&P 100 after 18 years (Fortune) → https://fortune.com/2026/09/08/nike-stock-plummets-sp500-market-cap-index/

The Further Mis-Adventures of Cliff Booth trailer: David Fincher directs Tarantino's script; IMAX Nov. 25, Netflix Dec. 23 (Variety) → https://variety.com/2026/film/news/the-further-mis-adventures-cliff-booth-trailer-brad-pitt-1236701901/

Timestamps:

0:00 Whoop fire alarm: Jason's dry-aged steak incident

1:30 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!

4:45 News: an OpenAI agent breached Australia's Medicare statistics portal

12:48 Scraper or hack? Australia's PM jumps into the AI safety debate

13:31 News: Google launches four TPUs into orbit for Project Suncatcher

18:27 Guest: Bryant Chou of PloyAI

20:07 AD: Paper is the legal backbone for thousands of startup founders and fund managers - including Launch. Use getpaper.ai/twist to get your cap table free for a year - or two years if you're leaving Carta.

21:11 Ploy's thesis: your website as your hardest working employee

27:05 Why a repeat unicorn founder went back to Y Combinator

38:55 The DOJ probe into a16z's Databricks and Fivetran board seats

44:57 "Nobody's thinking about you": Jason's stair story

45:17 Frontier models vs. your own model, and OpenAI's $2M YC token deal

54:04 News: Ando wants to replace Slack with agent-native chat

1:01:08 News: Tesla ramps Optimus to several hundred robots a week

1:04:48 Off-Duty: Jensen Huang tells Ezra Klein basic math may not matter

1:08:31 The MIT "Your Brain on ChatGPT" EEG study

1:09:57 Jason's five-part reset: sleep, diet, exercise, socializing, meditation

1:11:45 Off-Duty: Sydney Sweeney's Novig ad backlash

1:21:07 The Further Mis-Adventures of Cliff Booth trailer

1:23:41 Jason's first car: a 1970 Mustang GrandeSubscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com

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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 Slootman, Billy McFarland

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Today’s show:

Anthropic and OpenAI released cheaper models on the same day with Claude Opus 5.5 and GPT-6, and these VCs would still bet on open source. Jason brings on Dave McClure of Practical Venture Capital, Jeff Clavier of Uncork Capital, and Jenny Fielding of Everywhere Ventures to discuss the argument for open-weight models over the frontier labs.

Learn why median seed valuations have more than tripled since 2017. Why does Dave say it's a buyer's market for secondaries right now? PLUS, does Meta's Muse leave any room for Instinct, and why are fintech and healthcare suddenly out of favor?

Guests:

Dave McClure on X: https://x.com/davemcclure?lang=en Practical Venture Capital: https://practicalvc.com/

Jeff Clavier on X: https://x.com/jeff Uncorked Capital: https://uncorkcapital.com/

Jenny Fiedling on X: https://x.com/jefielding Everywhere Ventures: https://www.everywhere.vc/

Relevant Links:

Instinct reportedly seeking $1B at a $10B valuation (report via The Information) → https://cryptobriefing.com/ai-assistant-startup-instinct-targets-10b-valuation-in-new-funding-talks-report/

Meta's Muse, the agent the panel sees as Instinct's biggest threat, now on Mac → https://aiweekly.co/alerts/meta-ships-muse-for-mac-agent-now-acts-in-native-macos-apps

Trump calls Jensen Huang onstage at the All-In Summit → https://thenextweb.com/news/trump-phoned-jensen-huang-onstage-at-the-all-in-summit-to-call-ai-fear-a-hoax

AI-assisted intel error nearly triggered a US intercept of a Chinese ship (CNN via gCaptain) → https://gcaptain.com/ai-error-nearly-triggered-u-s-intercept-of-chinese-ship-cnn-reports/

Bernie Sanders' 50% AI sovereign wealth fund bill + Altman meeting (Fortune) → https://fortune.com/2026/06/18/bernie-sanders-ai-fund-bill-sam-altman-1000-payments/

Stanley Druckenmiller's AI-written WSJ op-ed (Axios) → https://axios.com/2026/08/26/stanley-druckenmiller-ai-writing-wsj-op-ed

Claude Opus 5.5 and GPT-6 Sol/Luna launch the same day with price cuts (SiliconANGLE) → https://siliconangle.com/2026/09/22/anthropic-releases-claude-opus-5-5-and-openai-counters-with-two-cheaper-gpt-6-models/

Zipline: LAUNCH's "miss," later backed through the syndicate → https://www.flyzipline.com/

Micro1 → https://www.micro1.ai/

Founder University → **https://www.founder.university/** [VERIFY]

The Syndicate: angel invest alongside LAUNCH (apply, waitlist) → **https://thesyndicate.com/**

Timestamps:

0:00 What seed rounds looked like then: Fitbit's $2M seed

2:38 Jenny's Techstars NYC years and the two-unicorn mug

6:10 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!

7:51 All-In Summit: Trump calls Jensen Huang onstage. Staged or not?

8:56 P(doom) roundtable + Dave's AI sovereign wealth fund prediction

10:08 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

13:35 The AI intel error that nearly triggered a US-China incident

17:44 "McClure's Law": a human with AI is the real risk

19:59 Odoo - The all-in-one business platform. Your first app is free! Get started today at https://Odoo.com/twist

21:37 Stripe + OpenRouter: an anti-fraud play, not a routing play?

23:07 Seed valuations: median $8M (2017) to $28M today

23:58 Instinct: $2.5B to a reported $10B in weeks

29:49 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.

44:01 Opus 5.5 vs. GPT-6 Sol: the same-day price war

46:51 Gun to your head: open-weight models or frontier labs?

51:00 Secondaries: the top 30 names vs. everyone else

52:30 Why fintech and healthcare are unloved (and Jason's Robinhood bet)

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Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland

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