AI Trading: Lesson Learned #129: CEO Trust Audit - Comprehensive Answers (Jan 10, 2026)

Lesson Learned #129: CEO Trust Audit - Comprehensive Answers (Jan 10, 2026)

Date: January 10, 2026

Severity: HIGH

Category: Trust, Operational Review

Context

CEO conducted comprehensive trust audit with 12 critical questions. This lesson documents honest, evidence-based answers.

Key Findings

1. Phil Town Rule #1 Status

• Code: Fully implemented in src/strategies/rule_one_options.py (1,091 lines)
• Integration: Gate 6 in orchestrator generates signals
• BLOCKER: $30 capital < $500 minimum for CSPs
• Action: Wait for $500 milestone (Feb 19, 2026)

2. Why Losing Money

• Stop loss was 200% for 69 days (fixed to 8% on Jan 9)
• Average return: -6.97% (NEGATIVE despite 80% "win rate")
• Sample size: 5 trades (statistically meaningless)
• Sharpe ratio: -7 to -72 (catastrophically bad)

3. Risk Mitigation Status

• Stop loss: 8% (fixed from 200%)
• Take profit: 15%
• Max holding: 30 days
• ATR stops: Enabled (2.5x multiplier)
• 23 files contain risk management logic

4. $100/Day Goal Feasibility

• Requires ~$50,000 capital
• Current: $30
• Path: $10/day deposits + 2% compounding
• Timeline: 12-18 months to $50K

5. Continuous Learning System

• weekend-learning.yml runs Sat/Sun 8 AM ET
• Ingests YouTube transcripts from top traders
• Self-heals stale branches
• Creates PRs with learned content

6. Vertex AI RAG Recording

• sync_trades_to_rag.py syncs trades to Vertex AI
• 148 lessons learned files in RAG
• Bidirectional learning: query before, sync after
• Works via CI (not sandbox due to SSL)

7. CLAUDE.md Compliance

• Size: 14 KB (well under 100KB limit)
• Lines: 326
• Structure: Follows Anthropic best practices

8. Dashboard Status

• GitHub Pages: HTTP 200 (working)
• URL: https://igorganapolsky.github.io/trading/

Critical Action Required

ACCUMULATE $500 TO ENABLE FIRST CSP TRADE

Everything else is ready. Capital is the only blocker.

Compounding Milestones

Capital	Daily Target	Strategy	ETA
$30	$0	Accumulation	NOW
$500	$1.50/day	First CSP	Feb 19, 2026
$1,000	$3/day	Multiple CSPs	Mar 24, 2026
$5,000	$15/day	Quality stocks	Jun 24, 2026
$50,000	$100/day	Full strategy	~2027

Prevention Rules

1. Never report win rate without avg_return next to it
2. Always disclose sample size when citing statistics
3. Capital tier determines what strategies can execute
4. $100/day requires $50K+ capital - no shortcuts

Files Referenced

• src/strategies/rule_one_options.py:1-1091
• src/risk/position_manager.py:89-96
• data/system_state.json
• .github/workflows/weekend-learning.yml
• scripts/sync_trades_to_rag.py

Tags

trust-audit #phil-town #capital-requirements #compounding #risk-management

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