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This Week in Startups

This Week in Startups

Jason Calacanis

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.

3730 - What VCs Really Think About Personal AI Agents | E2347
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  • 3730 - What VCs Really Think About Personal AI Agents | E2347

    This Week In Startups is made possible by: Plaud: http://Plaud.ai/twist Odoo: http://Odoo.com/twist Northwest Registered Agent: http://www.northwestregisteredagent.com/twistdomain Quo: https://www.quo.com/perks/twist Today’s show: A personal AI agent that’s still invite-only just hit a $10 billion valuation. Guest host Deedy Das of Menlo Ventures is joined by Kanu Gulati of Khosla Ventures, Chris Farmer of SignalFire, and Sheel Mohnot of Better Tomorrow Ventures to debate whether Instinct can beat Meta’s Muse, what they actually use their own agents for, and what breaks when everyone’s agent makes the same move. Plus we’re also talking about OpenAI’s math breakthroughs, the Factory vs. Cognition fight, and whether SaaS is still worth funding. Catch the whole debate on this week’s VC roundtable. Guests: Deedy Das on X: https://x.com/deedydas Menlo Ventures: https://menlovc.com Kanu Gulati on X: https://x.com/KanuGulati Khosla Ventures: https://www.khoslaventures.com Chris Farmer on X: https://x.com/chriswfarmer SignalFire: https://www.signalfire.com Sheel Mohnot on X: https://x.com/pitdesi Better Tomorrow Ventures: https://www.btv.vc Relevant Links: OpenAI’s 722 math manuscripts from an unreleased internal model → https://github.com/openai/math OpenAI’s earlier Navier–Stokes Millennium Prize result → https://openai.com/index/navier-stokes-solution/ Pramaana Labs, the Khosla-backed startup turning tax rules into provable logic → https://pramaanalabs.ai Logos Research, the Imperial College spinout verifying AI-written financial code → https://www.imperial.ac.uk/news/articles/2026/logos-research-plans-to-make-ai-reasoning-trustworthy-in-high-stakes-environments/ EvenUp, SignalFire’s AI company for personal injury law → https://www.evenuplaw.com/ WindBorne Systems, the Khosla-backed weather balloon company Kanu mentioned → https://windbornesystems.com Gokul Rajaram’s X Post: https://x.com/gokulr/status/2107851356019290569?s=20 micro1, the AI training data company Chris and LAUNCH backs → https://www.micro1.ai Vercel’s data on companies shifting to open-weight models → https://vercel.com/i/open-weight-models Instinct raises $1B at a $10B valuation (SiliconANGLE) → https://siliconangle.com/2026/09/28/everyday-personal-ai-assistant-startup-instinct-raises-1b-at-10b-valuation/ Meta introduces Muse, its personal AI agent → https://about.fb.com/news/2026/09/introducing-muse-personal-ai-agent/ Wajo, maker of the Fo agent Kanu uses → https://wajo.ai Factory’s CEO accuses his board adviser of spying for Cognition (TechCrunch) → https://techcrunch.com/2026/09/30/factory-ceo-just-accused-his-vc-board-advisor-of-spying-for-cognition/ xAI rents its Colossus 1 data center to Anthropic (Data Center Dynamics) → https://www.datacenterdynamics.com/en/news/musk-spacex-xai-is-actively-seeking-more-ai-compute-customers-following-anthropic-deal/ Bending Spoons agrees to buy Miro, weeks after Airtable → https://investors.bendingspoons.com/newsroom/bending-spoons-agrees-to-acquire-miro The FCC’s new rule on foreign-made robots → https://www.fcc.gov/covered-list-faqs-robots-inverters Timestamps: 0:00 VC roundtable with guest host Deedy Das 1:23 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! 2:11 OpenAI's math results and what's left to invest in 5:10 Formalizing taxes and code so AI can prove its work 6:37 Why science breakthroughs still need the real world 9:44 Odoo: The all-in-one business platform. Your first app is free! Get started today at https://Odoo.com/twist 10:54 Can startups compete with the labs on compute? 13:02 Private data and vertical AI as the moat 18:54 Would you invest in AI training data companies? 20:34 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 www.northwestregisteredagent.com/twistdomain 26:29 What a great founder looks like in the AI era 29:13 Quo (formerly OpenPhone) gives you a clean, modern way to handle every customer call, text, and thread all in one place. Try it free at https://quo.com/TWiST 34:35 Is Instinct worth $10 billion? 41:31 Can Muse reach a billion daily users? 44:49 Favorite personal agent use cases 49:06 What happens when everyone's agent makes the same call 53:17 Factory vs. Cognition and VCs backing rivals 1:03:49 Is SaaS still worth venture money? 1:09:49 Where the panel gets its information 1:14:45 What a seed fund means in 2026 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 Thank you to our partners: Check out all our partner offers: https://partners.launch.co/

    Thu, 08 Oct 2026
  • 3729 - 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/

    Wed, 07 Oct 2026
  • 3728 - 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

    Sat, 03 Oct 2026
  • 3727 - 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

    Thu, 01 Oct 2026
  • 3726 - 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  

    Mon, 28 Sep 2026
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