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  • An Untested Backup Is a Hypothesis

    My self-hosted AI assistant holds months of irreplaceable personal memory. War stories from making it actually survivable — silent failures, restore drills, and the discipline that turns backups from a checkbox into a guarantee.

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  • Building a Personal AI Chief of Staff — Notes From a Real Engagement

    I run a self-hosted AI chief-of-staff for myself. A friend who runs deal-flow at a family office asked for one. Here's the architecture, the build plan, and the design decisions that actually matter.

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  • Field-Testing a Wearable AI Recorder: What Survives Contact With Real Life

    I spent a week using a Plaud recorder as the capture layer for my self-hosted AI assistant — meetings, car rides, late-night voice memos. Here's what worked, what hallucinated, and the pipeline design lessons.

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  • Owning Your Social Graph Without Scraping

    I linked my Instagram followers and following to my personal CRM, classified 900 accounts into topical buckets, and built an unfollow workflow — using only official data exports. No scraping, no API abuse, no account risk.

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  • The Approval Gateway: Why My AI Assistant Can't Send an Email

    The most important component in my self-hosted AI assistant is the one that says no. Why every outbound action goes through a deterministic approval gate, and why that lives in code, not in a prompt.

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  • Why I Chose Hindsight for My AI Assistant's Memory

    Agent memory is where most personal-AI projects quietly fail. Why my self-hosted assistant uses Hindsight for semantic memory, what kinds of memory it actually captures, and the honest gotchas from running it in production.

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I'm Omar - Engineer. Tinkerer. Professional “what if” guy. This site is my digital twin — just less sleepy.

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