Lessons from a Startup Life

Lessons from a Startup Life

What LLMs Systems Can Infer About You

Doug Levin's avatar
Doug Levin
Dec 03, 2025
∙ Paid

The other day, I realized the LLM I was using (ChatGPT) remembered how I had signed off a letter I’d asked it to write earlier — and it genuinely surprised me.

For full disclosure, I regularly use ChatGPT 5.1, Perplexity Pro, Claude Opus 4.5, Copilot 365, and Mistral Medium 3 and occasionally use DeepSeek and Meta Llama 3.0.

Most LLM users simply assume …

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