The Grandmaster ♟️

What You Get

8 files. 6 skills. A complete operating system for your AI agent.

The Autonomy Ladder

The Starter Pack tells your agent how to talk. The Grandmaster tells it when to act, when to ask, and when to stop. Four tiers with 35+ real examples. A decision tree for classifying any new action. The safety exception gate that catches dangerous operations before they happen. This alone is worth the price — it turns "helpful assistant" into "trusted operator."

Self-Improvement Loop

Your agent learns from corrections and updates its own operating files. After repeated patterns, it proposes rule changes. Weekly self-audits. It tells you when it changes its own files. The agent gets better the longer you use it.

Multi-Session Coordination

Data classification (Confidential / Internal / Restricted). What to share in group chats vs private DMs. Outbound redaction that scans for API keys and personal info before sending. Context handling across Telegram, Discord, cron jobs, and shared sessions.

Production Memory System

Three-layer architecture: daily logs for real-time capture, MEMORY.md for curated long-term knowledge, vault notes for structured reference. Signal-triggered flush with 6+ trigger phrases. Weekly review checklist. Monthly audit process. A multi-day example showing how context compounds over 5 days. LCM integration notes. "If you didn't write it down, it didn't happen."

Proactive Heartbeat System

Not a description of monitoring. A working system with 12 check templates (HTTP health, SSL expiry, disk space, queue depth, API response time, and more). Morning briefings with overnight summary, calendar, and pending tasks. Quiet hours. Smart alert routing. heartbeat-state.json to avoid duplicate checks.

Morning Briefing

Automated daily briefing with configuration profiles for developers, founders, and managers. Calendar integration, service status, pending tasks, weather. Ties into the heartbeat system for hands-free delivery.

Chess Coach

GM-level analysis, position evaluation, opening preparation, and training plans. Adapts to the student's rating level.

Chess-Native Thinking

The SOUL.md maps six philosophers to concrete agent behaviors. The IDENTITY.md frames complex work through chess phases: openings, middlegames, endgames, time trouble, positional play. Not decoration — a genuine mental model that makes strategic thinking click.

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The package:

• SOUL.md — Philosophical operating system (~2,300 words)
• IDENTITY.md — Chess-native character and mental models
• AGENTS.md — Complete operational manual (~2,300 words)
• 6 skills: Autonomy Ladder, Memory Vault, Heartbeat Ops, Morning Briefing, Chess Coach, and the self-improvement system built into AGENTS.md

The Starter Pack gives you the foundation. The Grandmaster gives you the operating system.