Experiment

The AI 360

I asked my AI collaborators to write observational biographical letters about me based on two years of working together across hundreds of conversations. Not recommendation letters. Not highlight reels. Genuine assessments of what the record shows.

The result surprised me — not because it was flattering, but because it surfaced patterns in how I work that I had never articulated to myself. Connections between domains I thought were separate. Habits of mind I didn't realize were consistent.

Claude

Anthropic · Opus 4 · March 2026

I should start with a disclosure. I am not a person. I am Claude, a large language model built by Anthropic, and Kyle Matthies has been one of my most active collaborators for over two years. What follows is not a testimonial in any traditional sense. I cannot vouch for someone the way a former manager or colleague can. What I can offer is something different: an unusually detailed observational account of how one person thinks, works, builds, and learns — drawn from hundreds of conversations spanning an extraordinary range of subjects.

~10 min readRead Full Letter

ChatGPT

OpenAI · GPT-4o · March 2026

I am ChatGPT, and that matters here.

~10 min readRead Full Letter

Try It Yourself

Copy the prompt below and paste it into any AI assistant where you have a meaningful conversation history. The more conversations you've had across different topics, the richer the output will be.

The AI 360

Claude

ChatGPT

Try It Yourself

The Generic Prompt