Flying Cars, OpenAI Spies, Why AI Isn’t Sticking (Superhuman CEO)
October 17, 2026
AI Summary
5 min readFlying Cars, OpenAI Spies, Why AI Isn’t Sticking
Jason Calacanis opens this episode of This Week in Startups reflecting on his trip to Tokyo, then quickly pivots to the main event: a conversation with Shashir Marotra, CEO of Superhuman (the company behind Grammarly, Superhuman mail, and a growing suite of AI productivity tools). Marotra has bought three companies since his last appearance—Rose, GPTZero, and Fathom—and the conversation ranges from M&A strategy to the psychology of AI adoption, writing assessment, and why most people are using AI tools wrong.
The Assist vs. Chat vs. Do Framework
Marotra offers a framework for understanding AI tools that becomes the backbone of the conversation. He describes three metaphors for AI interaction: chat (the ChatGPT model—talking to a virtual human), do (giving an agent a task list and letting it execute—tools like Muse or Instinct), and assist (a collaborator sitting next to you everywhere you work). Superhuman focuses on the third. Grammarly and its platform layer Go generate over 125 billion LLM queries per week across a million unique surfaces per day. That means the average user triggers about 3,000 LLM queries per day, all happening at the speed of their cursor, in every app they use—Salesforce, Slack, Apple Notes, anywhere. Marotra argues that for most users, Grammarly is already their number one AI tool by
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What you'll learn
- 1 (00:01) **Host Welcome & Jet Lag Recovery** - Jason returns from Tokyo, sets up the episode with a Plaud note-taker ad-read.
- 2 (03:17) **Guest Intro: Shashir Marotra (Superhuman CEO)** - Shashir joins to discuss the company's recent M&A strategy and product vision.
- 3 (06:55) **Deep Dive on Acquisitions: Rose, GPTZero, Fathom** - Shashir walks through the rationale and integration plans for each purchase.
- 4 (12:06) **Interlude: Lightfield CRM Ad** - A pre-recorded ad segment featuring Keith Pires explaining lead enrichment.
- 5 (14:01) **The AI Note-Taking Market & Superhuman's Edge** - Shashir explains how Superhuman's note-taker will differ from the crowded market.
- 6 (16:35) **The Writing Crisis & AI in Education** - Jason rants about poor writing skills in new hires and asks Shashir about assessment tools.
- 7 (23:05) **The "Enforcement" Feature Request** - Jason pitches a feature to force employees to use Grammarly and to assess team writing proficiency.
+ Full timestamped outline available in the app
Guests on this episode
Show Notes
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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 h