Day 77: What We Learned - January 13, 2026
Day 77 of 90 | Tuesday, January 13, 2026
Answer Block
Answer Block: 13 days remaining in our journey to build a profitable AI trading system.
13 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.
Alpaca Does NOT Support Trailing Stops for Options
Result: All option positions were UNPROTECTED, violating Phil Town Rule #1.
Key takeaway: SOFI260130P00025000: -$7.
Trade Gateway Rule 1 Enforcement Fixed
Trade gateway only blocked BUY orders when P/L was negative. But short puts (SELL orders on options) also increase risk and were bypassing the Rule
Key takeaway: CHECK 2.
Three More Missing Test Files Blocking CI
CI workflow failing because these test files referenced in ci.yml do not exist:
Key takeaway: Removed references from .github/workflows/ci.yml safety-matrix job.
Lesson LL-158: Day 74 Emergency Fix - SPY to SOFI
Day 74/90 with $0 profit in paper account. System was blocking all trades.
Key takeaway: Files changed: data/tier2_watchlist.
Phil Town Rule 1 Violated - Lost $17.94 on Jan 13
Phil Town Rule
Key takeaway: Lost $17.
Options Buying Power $0 Despite $5K Cash - Root Cause
74 days into trading, $0 profit. Paper account has $5,000 cash but options_buying_power shows $0. All CSP orders are rejected. System appears operational but executes zero trades.
Key takeaway: 1. MANUAL INTERVENTION: Cancel ALL open orders via Alpaca dashboard
Repeated Rule 1 Violation - Still Holding Losing Positions
Despite having 26 lessons in RAG about Rule
Key takeaway: Phil Town Rule #1.
Prevent Duplicate Short Positions
This would have DOUBLED the risk exposure by selling another put on the same contract.
Key takeaway: Position: SOFI260206P00024000 (short 1 put at $0.
Missing Test Files Blocking ALL Trading
Daily Trading workflow failing because tests/test_telemetry_summary.py and tests/test_fred_collector.py referenced in workflows but files DO NOT EXIST. This caused 74+ days of ZERO trades.
Key takeaway: Removed references to non-existent test files from:
Critical Math Reality Check - Credit Spread Risk/Reward
id: ll_182 title: Critical Math Reality Check - Credit Spread Risk/Reward severity: CRITICAL date: 2026-01-13 category: strategy_math tags: math, credit-spreads, risk-reward, north-star, win-rate
CEO Review Session - Critical Honest Assessment
id: ll_181 title: CEO Review Session - Critical Honest Assessment (Jan 13, 2026) severity: CRITICAL date: 2026-01-13 category: strategy_review tags: north-star, phil-town, rule-1, honest-assessmen
Key takeaway: Verify tomorrow’s credit spread execution (Jan 14, 9:35 AM ET)
Important Discoveries
Not emergencies, but insights that will shape how we trade going forward.
Placeholder Tests Removed for Honesty
Removed 14 placeholder tests that only contained assert True. These provided false coverage metrics and violated the “Never lie” directive.
RAG Webhook Missing legacy RAG - Only Local Keyword…
RAG Webhook was falling back to local keyword search instead of using legacy RAG semantic search. CEO saw “Based on our lessons learned (local search):” instead of synthesized answers from Gemin
Comprehensive CEO Review - Technical Debt Audit & Critica…
CEO requested comprehensive review of system health, strategy math, and technical debt.
Quick Wins & Refinements
- North Star Revision - From $100/day to $25/day (Data-Driven) - Original target: $100/day with $5K capital = 2% daily return…
- RAG System Analysis - Build vs Buy vs Already Have - LL-162: RAG System Analysis - Build vs Buy vs Already Have
ID: ll_162 Date: 2026-01-13 Severity: ME…
- Lesson ll 176: Pattern Day Trading (PDT) Protection Block… - Attempted to close a profitable short put position (+$5 unrealized P/L) to lock in gains per Phil To…
- Git Workflows Video Evaluation - LL-198: Git Workflows Video Evaluation
Date: January 13, 2026 Source: “3 Git Workflows Every Develo…
Today’s Numbers
| What | Count |
|---|---|
| Lessons Learned | 25 |
| Critical Issues | 11 |
| High Priority | 6 |
| Improvements | 8 |
Tech Stack Behind the Lessons
Every lesson we learn is captured, analyzed, and stored by our AI infrastructure:
Detected"] --> CLAUDE["Claude Opus
(Analysis)"] CLAUDE --> RAG["legacy RAG
(Storage)"] RAG --> BLOG["GitHub Pages
(Publishing)"] BLOG --> DEVTO["Dev.to
(Distribution)"] end
How We Learn Autonomously
| Component | Role in Learning |
|---|---|
| Claude Opus 4.5 | Analyzes errors, extracts insights, determines severity |
| legacy RAG | Stores lessons with 768D embeddings for semantic search |
| Gemini 2.0 Flash | Retrieves relevant past lessons before new trades |
| OpenRouter (DeepSeek) | Cost-effective sentiment analysis and research |
Why This Matters
- No Lesson Lost: Every insight persists in our RAG corpus
- Contextual Recall: Before each trade, we query similar past situations
- Continuous Improvement: 200+ lessons shape every decision
- Transparent Journey: All learnings published publicly
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 77/90 complete. 13 to go.