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

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: 0:00 Intro 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 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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