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This Week in Startups

This Week in Startups

By: Jason Calacanis
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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.Jason Calacanis
Episodes
  • Why is Gen Z hates AI?

    Why is Gen Z hates AI?
    May 18 2026
    This Week In Startups is made possible by:Vanta - Vanta.com/TWISTSentry - Sentry.io/TWISTDeel - Deel.com/TWISTToday’s show:AI is the villain of the 2026 commencement cycle, with business luminaries — including Eric Schmidt — booed for discussing or praising the technology. As students graduate into a job market forcibly reshaped by AI, increasingly negative public polling on the potential impacts of artificial intelligence on society is clearly not missing the mark.Jason and Alex then discussed The Information’s reporting that Anthropic and OpenAI earn nearly 90% of all startup AI revenue, a Stanford student’s viral essay regarding their time at the university in a post-ChatGPT world, Flock Safety’s impressive (and worrying) web of cameras, and the upcoming Mark II AI bookmark. The episode closes with questions from our live audience!TWIST Links:Bounty website https://www.thisweekinstartups.com/bountySidebar bounty challenge https://www.notion.so/launch1/5K-Bounty-Create-Sidebar-App-for-Podcasts-34150ff313d280adbd8ed6204676513cAnnotated.com bounty challenge https://annotated.lovable.app/Timestamps:0:00 TWiST All-Stars summer lineup announcement2:43 Plaud: If your work depends on conversations — interviews, meetings, calls — you need a Plaud NotePin. You can check it out at https://Plaud.ai/twist and use code TWIST for 10% off!5:08 Eric Schmidt booed at University of Arizona commencement8:57 Why Gen Z feels "double-crossed" by AI leaders10:10 Deel - Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, get visas handled fast, and get back to building. Visit https://deel.com/twist to learn more.15:22 Is this AI's Vietnam moment? The anti-war parallel18:04 Theo Baker's NYT essay on Stanford's AI cheating culture19:24 Sentry - New users can get $240 in free credits when they go to https://sentry.io/twist and use the code TWIST22:30 Why Jason says everyone should start a company28:59 Anthropic + OpenAI capture 89% of AI startup revenue30:17 Vanta: Get $1000 off your SOC 2 at https://www.vanta.com/twist31:57 Are token sales a duopoly? Negative gross margins debate35:17 Risk of building app-layer startups on top of foundation models38:22 Inside Tracker bounty update: AI sidebar + Annotated.com41:18 Mark II: the $159 AI bookmark Alex wants49:31 Flock Safety solves Austin shooting via Manor PD53:39 DeFlock map and the geography of surveillance in Texas1:03:42 Noti Gang: AI for filing patents1:05:45 Noti Gang: Running AI models locally on Mac StudiosSubscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.comCheck out the TWIST500: https://www.twist500.comSubscribe to This Week in Startups on Apple: https://rb.gy/v19fcpFollow Alex:X: https://x.com/alexLinkedIn: ⁠https://www.linkedin.com/in/alexwilhelmFollow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanisCheck 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 McFarlandCheck out Jason’s suite of newsletters: https://substack.com/@calacanisFollow TWiST:Twitter: https://twitter.com/TWiStartupsYouTube: https://www.youtube.com/thisweekinInstagram: https://www.instagram.com/thisweekinstartupsTikTok: https://www.tiktok.com/@thisweekinstartupsSubstack: https://twistartups.substack.com
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    1 hr and 9 mins
  • The Self-Driving Startup Nobody Saw Coming | E2289

    The Self-Driving Startup Nobody Saw Coming | E2289
    May 15 2026
    This Week In Startups is made possible by:IM8 Health: IM8health.com/TWISTSquarespace: Squarespace.com/TWISTRender - Render.com/TWISTSelf-driving just stopped being a science problem and became an engineering challenge instead. That's the through-line of today’s double-header with the CEOs of two of the most important AV companies in the world — Wayve's Alex Kendall and Waabi's Raquel Urtasun. Between them: ~$2B raised in the last six months, Uber as a partner, Nissan and Volvo as OEMs, and a shared bet that end-to-end AI plus world models beats Waymo's city-by-city map-and-pray approach.If you want to understand the state of the self-driving industry beyond recent Waymo announcements, this is the episode for you.Guest Links:Wayve: wayve.ai/Waabi: http://waabi.ai/Alex Kendall https://www.linkedin.com/in/alexgkendall/Raquel Uratsun: https://www.linkedin.com/in/raquel-urtasun-298400139/Company Links:Wayve’s GAIA-2 world model: https://wayve.ai/thinking/gaia-2/Wayve’s 500 city roadshow: https://wayve.ai/thinking/ai-500-roadshow-500-cities/Wavye’s most recent funding round: https://wayve.ai/press/series-d/Waybe + Uber: https://wayve.ai/press/wayve-nissan-uber-robotaxi-collaboration/Waabi closed-loop simulator: https://waabi.ai/insights/waabi-worldWaabi + Volvo: https://waabi.ai/insights/waabi-and-volvo-autonomous-solutions-partner-to-jointly-develop-and-deploy-autonomous-transportation-solutionsWaabi + Uber: https://www.uberfreight.com/en-US/blog/uber-freight-and-waabi-introduce-industry-first-autonomous-truck-deployment-solutionTimestamps:0:00 Alex Kendall (Wayve) joins the show1:19 The contrarian bet on end-to-end AI and world models in 20173:05 What is a world model? GAIA-2 and GAIA-3 explained7:34 Sensor agnosticism: camera, radar, LiDAR and minimum bar for safety9:56 $1.5B raised — have we cracked self-driving?10:09 Render: Find out why 5 million developers are already using the all-in-one cloud platform, Render. Go to https://render.com/twist and apply for the Render Startup Program to get $500-$100,000 in free credits, depending on your stage and backers.20:38 Squarespace: Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST25:03 How consumers will actually pay: bundle, subscription, or free trial30:15 IM8 Health: Start feeling like your best self every day. Go to https://IM8health.com/twist and use the code TWiST to get a free welcome kit, five free travel sachets, and 10% off your order.35:59 Raquel Urtasun (Waabi) joins the show36:25 World models as controllable simulators for physical AI43:34 One AI brain across trucks, robotaxis, and beyond47:35 What changed in AI to make 2026 the deployment year52:28 Why Waabi raised $1B when they're capital-efficient58:52 Where Waabi is today: Volvo VNL Autonomous, Dallas-Houston, Uber Freight1:00:50 Per-mile pricing and the Driver-as-a-Service model1:07:20 Has Uber tried to buy Waabi? "Not for sale"Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.comCheck out the TWIST500: https://www.twist500.comSubscribe to This Week in Startups on Apple: https://rb.gy/v19fcpFollow Lon:X: https://x.com/lonsFollow Alex:X: https://x.com/alexLinkedIn: ⁠https://www.linkedin.com/in/alexwilhelmFollow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanisCheck 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 McFarlandCheck out Jason’s suite of newsletters: https://substack.com/@calacanisFollow TWiST:Twitter: https://twitter.com/TWiStartupsYouTube: https://www.youtube.com/thisweekinInstagram: https://www.instagram.com/thisweekinstartupsTikTok: https://www.tiktok.com/@thisweekinstartupsSubstack: https://twistartups.substack.com
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    1 hr and 13 mins
  • How Many Startups Will Survive OpenAI? | E2288

    How Many Startups Will Survive OpenAI? | E2288
    May 13 2026

    This Week In Startups is made possible by:Pilot -⁠ https://Pilot.com/TWIST⁠Grasshopper Bank -⁠ https://Grasshopper.bank/TWIST⁠Quo -⁠ https://Quo.com/TWiST⁠Plaud - ⁠https://Plaud.ai/twist⁠Anthropic just declared every unauthorized secondary sale of its stock "void" — naming Hiive, Forge, Sydecar, Upmarket, and others in a public hit list. Jason and Alex sit down with Jenny Fielding (Everywhere Ventures), Dave McClure (Practical VC), and Sam Lessin (Slow Ventures) to unpack what the AI lab’s move to limit secondary trades means for SPV operators, brokers, and the founders trying to keep control of their cap tables. Plus: a real story of a founder who returned a $15M Series A six months after closing because Claude was going to eat his startup, SaaS moats, and just what does it mean to be rich?Timestamps:0:00 Guest introductions0:48 Anthropic voids unauthorized SPV trades8:41 Accredited investor reform & the SEC sophisticated investor test8:58 Quo (formerly OpenPhone) - Quo 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/TWiST11:43 Naval's USVC closed-end fund as a workaround16:41 Plaud: If your work depends on conversations — interviews, meetings, calls — you need a Plaud NotePin. You can check it out at https://Plaud.ai/twist and use code TWIST for 10% off!17:48 Pro-rata rights battles: when Series A investors push seed investors out19:36 Grasshopper Bank: Time is money. Don't waste either. Go to https://grasshopper.bank/twist and get an exclusive $500 cash bonus just for opening an account.29:13 Pilot: Focus on your product, let Pilot handle your bookkeeping. Pilot provides the most reliable accounting, CFO, and tax services for startups and small businesses. Head to https://pilot.com/twist and get $1,200 off your first year.30:23 Storing wealth in stories vs. cash flows34:19 Cerebras and Fervo Energy IPOs — meaningful liquidity?37:54 Will SpaceX, Anthropic, OpenAI IPOs redistribute capital or compound it?45:58 The $15M Series A founder who returned the money because of Claude50:01 Should founders pivot or return capital when the world changes?56:43 OpenAI's $6.6B tender and Shruti Gandhi's viral SF cost-of-living tweet1:00:25 Intercom rebrands to Fin: the AI-first late-stage pivotSubscribe to the TWiST500 newsletter:⁠ https://ticker.thisweekinstartups.com⁠Check out the TWIST500:⁠ https://www.twist500.com⁠Subscribe to This Week in Startups on Apple:⁠ https://rb.gy/v19fcp⁠Follow Lon:X:⁠ https://x.com/lons⁠Follow Alex:X:⁠ https://x.com/alex⁠LinkedIn:⁠ ⁠https://www.linkedin.com/in/alexwilhelm⁠Follow Jason:X:⁠ https://twitter.com/Jason⁠LinkedIn:⁠ https://www.linkedin.com/in/jasoncalacanis⁠Check 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 McFarland⁠Check out Jason’s suite of newsletters:⁠ https://substack.com/@calacanis⁠Follow TWiST:Twitter:⁠ https://twitter.com/TWiStartups⁠YouTube:⁠ https://www.youtube.com/thisweekin⁠Instagram:⁠ https://www.instagram.com/thisweekinstartups⁠TikTok:⁠ https://www.tiktok.com/@thisweekinstartups⁠Substack:⁠ https://twistartups.substack.com⁠
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    1 hr and 25 mins
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