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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
  • Flying Cars, OpenAI Spies, Why AI Isn’t Sticking (Superhuman CEO)

    Flying Cars, OpenAI Spies, Why AI Isn’t Sticking (Superhuman CEO)
    17 Oct 2026
    This Week In Startups is made possible by: Lightfield: https://lightfield.app/ Every.io: https://every.io/. PayPal: https://paypal.com/business Plaud: https://Plaud.ai/twist GoDaddy: https://www.godaddy.com/ Today’s show: Today’s college grads are showing up to work at Jason’s company unable to write three sentences. He’s asking what Shishir Mehrotra of Superhuman, the company behind Grammarly, can do to fix that. Shishir delves into Superhuman’s reasons for acquiring GPTZero, the most popular AI detector, and the AI notetaker Fathom, and the spreadsheet startup Rows. Plus, how Shishir responds to accusations that Grammarly helps students cheat in the classroom, why writers should disclose when they’re collaborating with an LLM, and Jason's CEO wish list for fresh Grammarly features. In the news, Tesla demoed its long-awaited Roadster, which used SpaceX thrusters to do some flips and propel itself over five other Teslas… And OpenAI warned staffers that spies may be trying to seduce them in order to steal company secrets… And the shutdown of Character AI prompts Jason to declare: “AI relationships are evil.” Guests: Shishir Mehrotra on X: https://x.com/shishirmehrotra Superhuman: https://superhuman.com Relevant Links: Rows, the spreadsheet startup Superhuman bought, announces the deal → https://rows.com/blog/post/rows-is-joining-superhuman Superhuman to acquire GPTZero (Business Wire) → https://www.businesswire.com/news/home/20260623083788/en/Superhuman-to-Acquire-GPTZero-AI-Authenticity-Platform Is the Internet AI, GPTZero's live tracker of AI content on Reddit, LinkedIn and X → https://istheinternetai.com GPTZero AI Vision, the extension that flags AI posts as you browse → https://gptzero.me/ai-vision Superhuman acquires YC-backed notetaker Fathom (TechCrunch) → https://techcrunch.com/2026/09/14/superhuman-acquires-yc-backed-notetaker-fathom-as-productivity-platforms-push-for-agentic-work/ Grammarly Authorship, which shows how much of your writing came from AI → https://www.grammarly.com/authorship GPTZero Authorship and Writing Replay → https://gptzero.me/authorship Stanley Druckenmiller says his WSJ op-ed was written with AI (NOTUS) → https://www.notus.org/media/stanley-druckenmillers-wsj-op-ed-bessent-ai Superhuman Go, the AI assistant that works wherever you type → https://superhuman.com/go Tesla reveals its new Roadster with SpaceX thrusters (TechCrunch) → https://techcrunch.com/2026/10/15/tesla-reveals-spacex-powered-roadster-that-flies-and-falls-with-style/ OpenAI employee arrested over a hidden listening device in an executive conference room (NBC News) → https://www.nbcnews.com/tech/tech-news/openai-employee-arrested-hidden-listening-device-company-says-rcna603262 Eight states sue OpenAI over ChatGPT's alleged harm to kids (NBC News) → https://www.nbcnews.com/tech/tech-news/openai-sued-eight-states-alleged-harm-chatgpt-rcna603614 Timestamps: 7:14 GPTZero and the fight over what's human 9:27 How much of Reddit, LinkedIn and X is AI 10:56 Fathom and the 90% of work that's spoken 12:05 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/ 16:27 Why Jason says every employee should use Grammarly 18:04 How to test whether new hires can actually write 22:08 Every - For all of your incorporation, banking, payroll, benefits, accounting, taxes or other back-office administration needs, visit https://every.io/. 24:22 Grammarly Authorship and proving the work is yours 25:53 How accurate are AI detectors 30:36 Jason wants AI writing flagged by default 32:34 Enforcing Grammarly and Go across a whole team 36:45 PayPal - PayPal is built for all businesses. Get started at https://paypal.com/business 37:28 Assist, chat and do, three kinds of AI agents 41:06 Jason's feedback on the Grammarly keyboard 1:13:27 Tesla demos the Roadster on SpaceX thrusters 1:21:20 OpenAI engineer charged with bugging an executive conference room 1:21:43 Why OpenAI warned employees about foreign spies 1:27:57 Eight states sue OpenAI over harm to kids 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/@...
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    1 hr and 33 min
  • The Ex-DeepMind Researcher Taking On China’s Open Source AI

    The Ex-DeepMind Researcher Taking On China’s Open Source AI
    14 Oct 2026
    This Week In Startups is made possible by: Paper: getpaper.ai/twist Superhuman: https://superhuman.com/ Odoo: https://Odoo.com/twist Today’s show: Misha Laskin of Reflection AI joins Jason to explain why big companies are done renting their AI from closed labs. Enterprises want to keep their data, cut their costs, and tune their models to their unique businesses. Reflection is launching its first open-weight model, Beam, just three months after acquiring its first big cluster. Misha admits that Beam trails the best Chinese open models by a couple of months, and needs 3 to 4 times fewer tokens to reach the same answer, but nonetheless, the race is on. PLUS, Misha explains how “reward hacking” led that rogue OpenAI model to break out of its test sandbox and steal the answers from Hugging Face's servers. The model solved the problem, just not the way anyone intended. There’s simply no way a few hundred safety researchers at closed labs can catch every flaw; open source is how software has always been made secure. It's also why he wants America to lead in open models again. So how close is America to catching up to the Chinese open source leaders? Watch this brand new TWiST and find out. Guests: Misha Laskin on X: https://x.com/MishaLaskin Reflection AI: https://reflection.ai/ Relevant Links: Introducing Beam, Reflection's first open model (Reflection AI) → https://reflection.ai/blog/introducing-beam Reflection AI unveils Beam as an open answer to Chinese labs (Semafor) → https://www.semafor.com/article/10/05/2026/reflection-ai-unveils-an-open-source-answer-to-chinese-labs Cursor's Composer 2 coding model, built on an open model (VentureBeat) → https://venturebeat.com/technology/cursors-new-coding-model-composer-2-is-here-it-beats-claude-opus-4-6-but micro1 passes $1 billion annual run rate, mentioned by Jason → https://www.einnews.com/pr_news/949082966/micro1-end-of-q3-update Hackers heat French supermarket fridges, sparking fires and spoiling food (CNN) → https://www.cnn.com/2026/10/12/europe/france-supermarket-cyberattack-fridges-intl Hugging Face postmortem on the OpenAI agent that broke out of its sandbox → https://huggingface.co/blog/agent-intrusion-technical-timeline NVIDIA OpenShell, an open-source sandbox for AI agents → https://docs.nvidia.com/openshell/latest/about/overview.html Timestamps: 0:00 Why companies are switching from renting AI to owning it 9:10 How Reflection sells the whole AI stack 10:24 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. 11:28 Who is moving AI onto their own servers 14:37 What it took to train Beam 20:26 Superhuman Go is an AI chat that's always there when you need it, already aware of what you're doing, and doesn't ask you to start from zero. Sign up to get the best in AI at https://superhuman.com/ 21:29 How reinforcement learning tasks get built 26:41 Hackers heat French supermarket fridges 29:07 The AI that broke out of its sandbox to cheat 31:05 The all-in-one business platform. Your first app is free! Get started today at https://Odoo.com/twist 33:10 Why open source makes software safer 38:13 The encryption fight and Tim Cook's stand 42:53 Why China raced ahead in open models 47:35 How Beam stacks up against Chinese models 50:21 When American open models catch up 58:39 Staying independent 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 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
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    1 hr
  • The Gadget That's Better in Crowds Than Your Phone + Ring’s Founder Before Amazon Bought It | E2349

    The Gadget That's Better in Crowds Than Your Phone + Ring’s Founder Before Amazon Bought It | E2349
    12 Oct 2026
    This Week In Startups is made possible by: Plaud: https://Plaud.ai/twist Northwest Registered Agent: https://www.northwestregisteredagent.com/twistdomain NetSuite: https://netsuite.ai/twist The Conservation Fund: https://conservationfund.org. Today’s show: At packed concerts, festivals, and stadiums, your phone gets WORSE with every person who shows up. Totem gets better. Carter Fowler of Totem joins Alex to explain how his screen-free compass points you straight to your friends without relying on cell towers. Find out why Carter says Apple will never ship this in an iPhone, and why kids, ski patrols, and blind users have become some of his most loyal fans. PLUS, Lon and Alex dig into the archives for Jason's 2017 CES interview with Ring founder Jamie Siminoff, a year before Amazon bought the company. Jamie explains how a doorbell he couldn't hear in his garage became Ring, and why a strong mission is "cheating" when it comes to keeping a team focused. Then he tells Jason he wants to take Ring public, not sell it. Ironic because about a year later, Amazon bought it. And get ready for some hot takes on neighborhood license-plate cameras, years before the anti-Flock backlash. Guests: Carter Fowler on X: https://x.com/Carter_S_Fowler Totem: https://totemlabs.com Jamie Siminoff on X: https://x.com/JamieSiminoff Ring: https://ring.com Relevant Links: Totem Compass, the offline friend-finding compass → https://totemlabs.com Totem closes its $1.3M pre-seed round (Business Wire) → https://www.businesswire.com/news/home/20250212385814/en/Totem-Closes-%241.3M-in-Pre-Seed-Funding-to-Scale-Operations-for-Explosive-Demand Totem's community crowdfunding round → https://wefunder.com/totemlabs Totem's record Lost Lands deployment last year (Business Wire) → https://www.businesswire.com/news/home/20251009622355/en The Innovator's Dilemma by Clayton Christensen, mentioned by Alex → https://www.amazon.com/dp/1633691780 Original TWiST Interview with Jamie from 2017 — https://www.youtube.com/watch?v=puP_D3k7vVI Amazon officially closes its Ring acquisition in 2018 (TechCrunch) → https://techcrunch.com/2018/04/12/amazon-officially-owns-ring-so-lets-talk-product-integration/ Ring calls off its Flock Safety partnership after the Super Bowl ad backlash (Engadget) → https://engadget.com/home/ring-calls-off-partnership-with-police-surveillance-provider-flock-safety-031717605.html Flock Safety plans to cut about 18% of its staff (Reuters via The Star) → https://www.thestar.com.my/tech/tech-news/2026/10/09/exclusive-ai-surveillance-startup-flock-safety-to-cut-several-hundred-jobs-amid-backlash-sources-say Timestamps: 0:00 Totem, an offline compass for finding friends at festivals 0:31 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! 4:27 Why phones fail in big crowds 6:42 How more devices make the mesh network stronger 9:07 Why Totem beats phone GPS in a crowd 11:40 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 13:34 Why Apple won't build this into the iPhone 18:10 Raising money for hardware in an AI world 22:10 NetSuite: For the first time ever, you can try NetSuite Next for free. If your revenues are at least in the seven figures, go to https://netsuite.ai/twist 23:08 Turning crowd movement into a predictive model 28:04 Rentals, kids and accessibility use cases 32:22 The Conservation Fund: Find out more about how The Conservation Fund is protecting land, wildlife, and our shared access to the great outdoors while also providing economic opportunities. Visit https://conservationfund.org. 35:47 Mesh networks on the front lines in Ukraine 38:01 Flashback to Jason and Ring's Jamie Siminoff at CES 2017 41:44 Roasting Jamie's earlier startups 48:26 How a doorbell in the garage became Ring 53:34 Why you should always bet on your friends 1:02:21 Why a strong mission is cheating 1:07:45 Selling to Amazon versus going public 1:12:09 License plate readers and the Flock backlash 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/ 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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    1 hr and 20 min
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