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

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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:x.com/shishirmehrotra Superhuman:superhuman.com

Relevant Links:

Rows, the spreadsheet startup Superhuman bought, announces the deal →rows.com/blog/post/rows-is-joining-superhuman

Superhuman to acquire GPTZero (Business Wire) →businesswire.com/news/home/20260623083788/en/S…

Is the Internet AI, GPTZero's live tracker of AI content on Reddit, LinkedIn and X →istheinternetai.com

GPTZero AI Vision, the extension that flags AI posts as you browse →gptzero.me/ai-vision

Superhuman acquires YC-backed notetaker Fathom (TechCrunch) →techcrunch.com/2026/09/14/superhuman-acquires-…

Grammarly Authorship, which shows how much of your writing came from AI →grammarly.com/authorship

GPTZero Authorship and Writing Replay →gptzero.me/authorship

Stanley Druckenmiller says his WSJ op-ed was written with AI (NOTUS) →notus.org/media/stanley-druckenmillers-wsj-op-…

Superhuman Go, the AI assistant that works wherever you type →superhuman.com/go

Tesla reveals its new Roadster with SpaceX thrusters (TechCrunch) →techcrunch.com/2026/10/15/tesla-reveals-spacex…

OpenAI employee arrested over a hidden listening device in an executive conference room (NBC News) →nbcnews.com/tech/tech-news/openai-employee-arr…

Eight states sue OpenAI over ChatGPT's alleged harm to kids (NBC News) →nbcnews.com/tech/tech-news/openai-sued-eight-s…

Timestamps:

Intro

GPTZero and the fight over what's human

How much of Reddit, LinkedIn and X is AI

Fathom and the 90% of work that's spoken

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 lightfield.app

Why Jason says every employee should use Grammarly

How to test whether new hires can actually write

Every - For all of your incorporation, banking, payroll, benefits, accounting, taxes or other back-office administration needs, visit every.io.

Grammarly Authorship and proving the work is yours

How accurate are AI detectors

Jason wants AI writing flagged by default

Enforcing Grammarly and Go across a whole team

PayPal - PayPal is built for all businesses. Get started at paypal.com/business

Assist, chat and do, three kinds of AI agents

Jason's feedback on the Grammarly keyboard

Tesla demos the Roadster on SpaceX thrusters

OpenAI engineer charged with bugging an executive conference room