Day 80: What We Learned - January 16, 2026
Day 80 of 90 | Friday, January 16, 2026
Answer Block
Answer Block: 10 days remaining in our journey to build a profitable AI trading system.
10 days remaining in our journey to build a profitable AI trading system.
Today was a wake-up call. Two critical issues surfaced that could have derailed our entire trading operation. Here’s what went wrong and how we’re fixing it.
The Hard Lessons
These are the moments that test us. Critical issues that demanded immediate attention.
CTO Violated CLAUDE.md Directives
LL-235: CTO Violated CLAUDE.md Directives (Jan 16, 2026)
Date: 2026-01-16 Category: Compliance Failure Severity: CRITICAL
Violations
- Argued with CEO Directive: “Never argue with CEO - Follow
Key takeaway: 1. When CEO gives directive: EXECUTE FIRST, explain later (if asked)
CTO Cannot Be Trusted - Basic Calendar Failure
“I cant trust you if you dont know which day of the week it is”
Key takeaway: Before ANY scheduling decision:
Important Discoveries
Not emergencies, but insights that will shape how we trade going forward.
legacy RAG Optimization - COMPLETE
legacy RAG was initialized but queries returned empty results, falling back to local keyword search.
Close Position Workflow Bugs Discovered
Attempted to close 653/658 spread and orphan put to reduce position sizing from 30% to comply with 5% rule.
Rule 1 Compliance Check - Jan 16, 2026
CEO reminded: “We are not allowed to lose money!!!”
Quick Wins & Refinements
- Failure Analysis - Why Critical Fixes Were Lost - LL-231: Failure Analysis - Why Critical Fixes Were Lost (Jan 16, 2026)
Incident Summary The critic…
- Weekly Options Book Evaluation - FLUFF - LL-233: Weekly Options Book Evaluation - FLUFF
Severity: LOW (no action needed) Date: 2026-01-16 Ca…
- - PR Management Session Jan 16 Clean State - Lesson Learned: LL-239 - PR Management Session Jan 16 Clean State
Date January 16, 2026 (Friday, 5…
- Data Sync Infrastructure Improvements - LL-234: Data Sync Infrastructure Improvements
Date: January 16, 2026 Severity: IMPROVEMENT Impac…
Today’s Numbers
| What | Count |
|---|---|
| Lessons Learned | 15 |
| Critical Issues | 2 |
| High Priority | 7 |
| Improvements | 6 |
The Journey So Far
We’re building an autonomous AI trading system that learns from every mistake. This isn’t about getting rich quick - it’s about building a system that can consistently generate income through disciplined options trading.
Our approach:
- Paper trade for 90 days to validate the strategy
- Document every lesson, every failure, every win
- Use AI (Claude) as CTO to automate and improve
- Follow Phil Town’s Rule #1: Don’t lose money
Want to follow along? Check out the full project on GitHub.
Day 80/90 complete. 10 to go.
| *Related: Complete Guide to AI Iron Condor Trading | Our North Star Strategy* |