This Week in Startups

Jason Calacanis
  • 4.2 (1.3K)
  • Technology
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Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology. He also interviews the world's greatest founders, operators, investors, and innovators.

  1. 1h ago

    Jason Mentors The Next Generation + Why AI Is Bad at Teaching (Aristotle Interview) | E2346

    This Week In Startups is made possible by: Vanta: https://www.vanta.com/twist DigitalOcean: https://do.co/twist Sentry: http://sentry.io/twist Plaud: http://Plaud.ai/twist Today’s show: The smarter AI gets, the more it just does the work for you, and the less helpful it becomes as a tutor. Shan Reddy of Aristotle joins Jason to demo a voice-first tutor built to run a session the way a $200-an-hour human tutor would. We also dive into why frontier models are trained to hand you answers rather than build real understanding. PLUS, in Ask Jason, an incoming Fordham student (Jason’s alma mater!) wants to prepare for a career in finance. Plus, David from NYU calls back and wants to discuss what everyone would do with $500K in free money. Then, why does Jason think the Doomerism is coming from inside the AI labs? Guests: Shan Reddy on X: https://x.com/rshanreddy Aristotle: https://www.heyaristotle.com/ Relevant Links: Shoe Dog by Phil Knight → https://en.wikipedia.org/wiki/Shoe_Dog Something Like an Autobiography by Akira Kurosawa → https://en.wikipedia.org/wiki/Something_Like_an_Autobiography Einstein: His Life and Universe by Walter Isaacson, which Dovid is reading now → https://en.wikipedia.org/wiki/Einstein:_His_Life_and_Universe Gartner, Jason's example of firms doing research on behalf of corporations → https://www.gartner.com/ "Religious Scholars Met With Anthropic. What They Heard Stunned Them." by Elizabeth Dias, The New York Times, Sept. 29, 2026; the story Lon brings up → https://www.inquirer.com/news/nation-world/religious-leaders-met-with-anthropic-20260930.html David Sacks accuses Anthropic of a "regulatory capture strategy based on fear-mongering"; the line Lon references (Bloomberg Law) → https://news.bloomberglaw.com/artificial-intelligence/anthropic-is-running-a-strategy-based-on-fear-mongering-sacks Aristotle's $5M seed round (PR Newswire) → https://www.prnewswire.com/news-releases/aristotle-secures-5m-to-replace-the-chatbot-with-high-dosage-ai-tutoring-for-students-302880500.html "The 2 Sigma Problem" by Benjamin Bloom (1984), original paper → https://web.mit.edu/5.95/readings/bloom-two-sigma.pdf Journal record (Educational Researcher / SAGE) → https://journals.sagepub.com/doi/10.3102/0013189X013006004 NYC's AI moratorium through 8th grade (ABC News) → https://abcnews.com/Technology/new-york-city-public-schools-banning-ai-middle/story?id=136134872 Alpha School → https://www.alpha.school Brilliant's origin story at the LAUNCH Festival (NPR) → https://www.npr.org/blogs/alltechconsidered/2013/07/23/203677692/giving-brightest-kids-the-cram-school-experience-online Timestamps: 0:00 Live Ask Jason kicks off 0:14 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! 0:56 Fordham-bound caller asks how to break into finance in the AI era 5:15 Jason's gift: read one biography a month 9:22 Vanta: Get $1000 off your SOC 2 at https://www.vanta.com/twist 11:22 Returning caller David: what would you do with $500K? 19:09 DigitalOcean: Want to see what building on a true AI-native platform looks like? Head to https://do.co/twist to start building on DigitalOcean's AI-Native Cloud today - and cut your AI workload costs by up to 50%. 23:56 Bringing an AI protein folding tool into drug discovery 26:35 How to do customer discovery with big companies 29:00 The "dark arts" of market research and corporate intelligence 29:29 Sentry: Your team should be focused on shipping features - not chasing down bugs. New users can get $240 in free credits when they go to https://sentry.io/twist and use the code TWIST26 32:59 Is AI fear a dark PR campaign? 34:17 Anthropic meets with religious scholars 40:01 Are AI labs living through an Oppenheimer moment? 42:06 Why we need to talk about AI's upside in education 43:47 Sean Ready, co-founder and CEO of Aristotle, joins 44:58 Why AI models are getting worse at teaching 47:09 Aristotle demo: a voice AI tutor for AP Calculus 50:29 Predicting the next best teaching action 53:32 Bloom's two sigma problem and one-on-one tutoring 54:38 Aristotle's business model and pricing 57:09 Building a tutoring harness vs. relying on frontier labs 1:00:21 Why dyslexic students love Aristotle 1:01:56 Hand-grading thousands of hours of tutoring sessions 1:04:22 Socialization, classrooms and the future of public education 1:08:32 Where to try Aristotle and open roles 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/

  2. 4d ago

    Inside The Startup Building Uncensored AI (Abliteration AI) | EP 2345

    This Week In Startups is made possible by: Every.io: http://every.io/ Northwest Registered Agent: https://www.northwestregisteredagent.com/twistdomain Odoo: http://Odoo.com/twist Plaud: http://Plaud.ai/twist Today’s show: What can AI do with the guardrails OFF? Devon Thomas of Abliteration.ai thinks defenders should have access to the same kinds of tools, rather than having one hand tied behind their backs. Then, on Ask Jason, learn what AI means for the billable hour from a legal-tech founder. PLUS, are AI microdramas a real ecosystem or a fad, and does AI finally make solo founders fundable? Guests: Devon Thomas on X: https://x.com/founderengineer Abliteration: https://abliteration.ai/ Relevant Links: Abliteration.ai on a16z speedrun — the accelerator Jason congratulated Devon on → https://speedrun.a16z.com/companies/abliteration TechCrunch: "Abliteration.ai is making a business out of removing AI guardrails" — the coverage behind the recent attention → https://techcrunch.com/2026/09/03/abliteration-ai-is-making-a-business-out-of-removing-ai-guardrails/ Abliteration.ai press page → https://abliteration.ai/press Anthropic Frontier Red Team: "GLM-5.3 and the spread of advanced cyber capabilities" — the blog Devon cited on how capable abliterated GLM-5.3 is → https://www.anthropic.com/research/glm-5-3-and-the-spread-of-advanced-cyber-capabilities CNBC: Trump's executive order renaming AI "super intelligence," signed the same day → https://www.cnbc.com/2026/09/29/trump-ai-super-intelligence.html Nextgov/FCW: OpenAI agents accessed Census and SEC data — detail on the dozens of organizations OpenAI notified → https://www.nextgov.com/cybersecurity/2026/09/openai-says-its-advanced-models-may-have-gone-after-government-websites/416250/ Financial Times: "AI wrecking ball fractures billable-hour fee model" Seedance 2.5 — ByteDance's video model Bruno asked about → https://technode.com/2026/07/31/bytedance-launches-seedance-2-5-video-generation-model/ Pixar / Toy Story — the CGI "Toy Story moment" Jason expects for AI video → https://en.wikipedia.org/wiki/Toy_Story Practi — Mathew's platform for helping law firms move from hourly billing to subscriptions → https://practi.ai/hello Timestamps: 0:00 What http://Abliteration.ai does, and who the frontier labs are shutting out 2:44 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! 2:56 Why defenders don't get the attackers' tools 4:16 "Inversion of control": letting customers set their own guardrails 6:47 Who's liable? The hammer analogy and the White House self-regulation pact 10:11 Every: For all of your incorporation, banking, payroll, benefits, accounting, taxes or other back-office administration needs, visit https://every.io. 13:10 Why AI labs publicize their scariest hacks 18:52 Customers: from cyber startups to Fortune 500 CISOs 19:56 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 http://northwestregisteredagent.com/twistdomain 24:41 Chinese image and video models 27:20 Why most businesses still barely use AI 29:02 Ask Jason begins 29:24 Mathew Kerbis (Practi): What does AI do to the billable hour? 30:16 Odoo: The all-in-one business platform. Your first app is free! Get started today at https://Odoo.com/twist 32:45 Will subscriptions replace hourly billing? 37:27 Bruno Vilela: Are AI microdramas an ecosystem or a fad? 39:35 Lon's microdrama pitch to Snapchat and TikTok's PineDrama 48:09 Josh Ezell: Does AI change the bias against solo founders? 49:26 Jason's three-two-one framework and the risks founders must eliminate 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 Slootman, Billy McFarland Follow TWiST: Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin Instagram: https://www.instagram.com/thisweekinstartups TikTok: https://www.tiktok.com/@thisweekinstartups Substack: https://twistartups.substack.com

  3. 6d ago

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

    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 Slootman, Billy McFarland Follow TWiST: Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin Instagram: https://www.instagram.com/thisweekinstartups TikTok: https://www.tiktok.com/@thisweekinstartups Substack: https://twistartups.substack.com

  4. Sep 28

    Jason’s Put a $5K Bounty on His Dream Chrome Extension | E2338

    This Week In Startups is made possible by: Every.io: http://every.io/ Northwest Registered Agent: www.northwestregisteredagent.com/twistdomain Sentry: http://sentry.io/twist 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 Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com Check out the TWIST500: https://www.twist500.com Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp Follow Lon: X: https://x.com/lons Follow Jason: X:   / jason   LinkedIn:   / jasoncalacanis

  5. Sep 28

    The 5 Companies Apple Must Buy

    This Week In Startups is made possible by: PayPal - https://paypal.com/business Northwest Registered Agent - https://www.northwestregisteredagent.com/twistdomain Odoo - https://Odoo.com/twist 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: 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 Slootman, Billy McFarland Follow TWiST: Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin Instagram: https://www.instagram.com/thisweekinstartups TikTok: https://www.tiktok.com/@thisweekinstartups Substack: https://twistartups.substack.com

  6. Sep 25

    A rogue OpenAI agent hacked Australia’s government. Does this matter? | E2342

    This Week In Startups is made possible by: https://lightfield.app/ http://getpaper.ai/twist https://conservationfund.org/ http://Plaud.ai/twist https://www.athena.com/jcal 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 Check out the TWIST500: https://www.twist500.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 Slootman, Billy McFarland Subscribe to our Substack Newsletters! TWiST: https://twistartups.substack.com/ TWiAI: https://www.thisweekinai.ai/ TWiVC: https://thisweekinvc.substack.com/ Follow TWiST: Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin Instagram: https://www.instagram.com/thisweekinstartups TikTok: https://www.tiktok.com/@thisweekinstartups Substack: https://twistartups.substack.com

  7. Sep 23

    VCs Would Bet on Open-Source AI Over OpenAI and Anthropic | E2341

    This Week In Startups is made possible by: Northwest Registered Agent: https://www.northwestregisteredagent.com/twistdomain Odoo: http://Odoo.com/twist Rippling: http://Rippling.ai/twist Plaud: http://Plaud.ai/twist Harmonic: http://harmonic.ai/ 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) Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com Check out the TWIST500: https://www.twist500.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 Thank you to our partners: (0:00) PARTNER - AD BLURB (0:00) PARTNER - AD BLURB (0:00) PARTNER - AD BLURB 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 Subscribe to our Substack Newsletters! TWiST: https://twistartups.substack.com/ TWiAI: https://www.thisweekinai.ai/ TWiVC: https://thisweekinvc.substack.com/ Follow TWiST: Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin Instagram: https://www.instagram.com/thisweekinstartups TikTok: https://www.tiktok.com/@thisweekinstartups Substack: https://twistartups.substack.com

  8. Sep 21

    Elon's New Hyperloop, Trump's AI Rename, and a Model That Won't Talk | E2340

    This Week In Startups is made possible by: Vanta: https://www.vanta.com/twist DigitalOcean: http://do.co/twist Lightfield: https://lightfield.app/ Plaud: http://Plaud.ai/twist Today’s show: Elon revives the Hyperloop, promising a 30-minute commute between Austin and San Antonio. It's the kind of project that could reshape how Texans think about getting between two major cities entirely. Then, Jason and Lon explain why this pitch is different from the other Boring Company tunnels. Learn why President Trump wants to rename artificial intelligence itself and launch an "AI Force." It's a move that could reshape how the government talks about AI policy going forward. PLUS, a new startup's model refuses to write a single word of text, and it is 5 to 18 times faster with better accuracy. It's a completely different approach to how AI agents make decisions, and it might be a preview of where the industry heads next. Relevant Links: "Elon Musk's latest Boring Company pitch involves a Hyperloop between Austin and San Antonio" → https://techcrunch.com/2026/09/20/elon-musks-latest-boring-company-pitch-involves-a-hyperloop-between-austin-and-san-antonio/ The Boring Company → https://www.boringcompany.com/ Elon Musk's original 2013 Hyperloop white paper → https://www.tesla.com/sites/default/files/blog_images/hyperloop-alpha.pdf Trump's Truth Social post proposing "Superior/Extreme/Supreme Intelligence" and announcing an AI Force and AI czar → https://www.unite.ai/trump-proposes-renaming-artificial-intelligence-announces-ai-force/ TechCrunch: "Trump says it's time to rebrand AI with a new name — and he's also creating an AI Force" → https://techcrunch.com/2026/09/19/trump-suggests-rebranding-ai-with-a-new-name-says-hes-also-creating-an-ai-force/ Vercel AI Open vs Closed Source Volume Chart → https://vercel.com/ai-gateway/leaderboards/models TypeSafe AI — makers of Jev, the "System One Model" → https://typesafe.ai/ TypeSafe AI blog: "Introducing System One Models & Jev" → https://typesafe.ai/blog/introducing-system-one-models-and-jev GeekWire: "Amazon blocks Meta's Muse AI assistant in new standoff over agentic shopping" → https://www.geekwire.com/2026/amazon-blocks-metas-muse-ai-assistant-in-new-standoff-over-agentic-shopping/ Meta's Muse — the AI agent Amazon blocked from shopping on its site → https://www.meta.ai/ "Meta's Dina Powell McCormick: The Case for Data Centers, Backlash, AI Job Boom & Meta's Future" (All-In Podcast, YouTube) — the clip discussed on the show → https://www.youtube.com/watch?v=qp2IbgJ5Z-8 Robocurve's RoboHarm report — the robot-safety benchmark discussed on air → https://robocurve.org/roboharm/ RoboHarm on GitHub (tasks, protocol, and tooling) → https://github.com/robocurve/roboharm Timestamps: 0:00 Elon Musk revives the Hyperloop: a 30-minute Austin–San Antonio tunnel 1:03 A brief history of Hyperloop and the white paper 8:56 Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist 16:46 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! 20:32 DigitalOcean - Head to https://do.co/twist to start building on DigitalOcean's AI-Native Cloud today — and cut your AI workload costs by up to 50%. 21:40 News: Trump proposes an "AI Force," an AI czar, and renaming AI itself 22:49 "Get back to work, nerds" 30:22 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 31:56 TypeSafe's Jev, a "System One" model built to decide, not chat 39:49 Amazon blocks Meta's Muse AI agent 49:57 Dina Powell McCormick's tense All-In Summit exchange with Jason 1:02:38 Off-Duty: Robocurve's RoboHarm benchmark Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com Check out the TWIST500: https://www.twist500.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 Slootman, Billy McFarland Check out Jason’s suite of newsletters: https://substack.com/@calacanis Follow TWiST: Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin Instagram: https://www.instagram.com/thisweekinstartups TikTok: https://www.tiktok.com/@thisweekinstartups Substack: https://twistartups.substack.com

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Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology. He also interviews the world's greatest founders, operators, investors, and innovators.

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  • Creator
    Jason Calacanis
  • Years Active
    2009 - 2026
  • Episodes
    1.5K
  • Rating
    Explicit
  • Copyright
    © Jason Calacanis
  • Show Website
    This Week in Startups

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