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Beware what you tell your AI chatbot. It’s not a shrink – it’s a snitch | Arwa Mahdawi
Arwa Mahdawi · 2026-05-13 · via Hacker News - Newest: "AI"

The hottest new read of 2026 may well be The Secret Diary of Greg Brockman, Aged 38¾. It’s got everything: feuding billionaires, scheming CEOs and a perhaps somewhat unreliable narrator. You won’t find it in the library, but you can watch Brockman, a co-founder and president of OpenAI, being forced to read the juiciest bits out loud in court.

Before you ask ChatGPT to explain, here’s the backstory: Elon Musk is in a legal battle with Brockman and the OpenAI CEO, Sam Altman. Musk, a former board member of OpenAI, is accusing the men of violating the AI firm’s founding agreement by turning it into a for-profit entity. Meanwhile, Altman et al are arguing Musk is just upset he’s not in control of the company and wants to bring down his competition.

Helpfully for Musk, Brockman kept a diary during the company’s founding years; this has become central to the case. In one heavily cited extract, Brockman writes: “Financially what will take me to $1B?” Another scrutinised passage: “It’d be wrong to steal the non-profit from [Musk]. to convert to a b-corp without him. that’d be pretty morally bankrupt. and he’s really not an idiot.” (He may have been lusting after billions, but his sentence structure suggests Brockman is ambivalent about capitalism – or at least capitals.)

Look, I’m not an expert in crime management, but I’m pretty sure there are certain thoughts you shouldn’t share with Dear Diary. Even Brockman’s tech bro peers are aghast at his journal-maxxing. “I love the guy, but what … is he thinking?” David Friedberg, a co-host of the All-In podcast, said on a recent episode. “You’re just sitting here at home, like, let me write about the crime I’m committing … and by the way, let me never delete it.” Alleged crime, David, alleged.

Not a lot of people are keeping journals laying out potentially problematic corporate manoeuvres. However, millions of people are using tools such as ChatGPT as a sort of therapist or digital confession box; a place to share private or half-formed thoughts. “Within the next decade,” one lawyer told Axios, “the diary equivalent will be standard discovery in every major executive litigation in the country.”

What does this mean? It means you shouldn’t trust a chatbot with your secrets because, as a number of recent cases demonstrate (including one where a former NFL player allegedly asked ChatGPT for help after he killed his girlfriend), conversations with AI are admissible in court. Even if you don’t expect any legal trouble, you should be wary about sharing your sensitive information: most chatbot conversations are not private, and may be retained indefinitely and shared with other humans. Your AI chatbot is not a shrink – it’s a snitch.