Day 84 of 90 | Tuesday, January 20, 2026

Answer Block

Answer Block: 6 days remaining in our journey to build a profitable AI trading system.

6 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.

Trading Crisis - System Stuck for 7 Days

-

CI Failure Due to Legacy SOFI Position

  1. CI failed at 15:41 UTC with test test_positions_are_spy_only failing

Key takeaway: CLAUDE.

System Blocked But No Auto-Cleanup Mechanism

The trading system correctly blocked new trades due to 30% risk exposure (3 spreads when max is 1), but there was NO automated mechanism to close excess positions. Result: 0 trades on Jan 20, 2026

Key takeaway: If a system can detect a violation, it must also have an automated path to RESOLVE that violation.

Important Discoveries

Not emergencies, but insights that will shape how we trade going forward.

SOFI PDT Crisis - SPY ONLY Violation

A SOFI short put position (SOFI260213P00032000) was opened at 14:35 UTC, violating the “SPY ONLY” directive in CLAUDE.md. The position is now -$150 unrealized and cannot be closed until tomorrow due t

PDT Protection Blocks SOFI Position Close

SOFI260213P00032000 (short put) cannot be closed due to PDT (Pattern Day Trading) protection.

Quick Wins & Refinements

  • Exceptional Daily Profit - Strategy Validated - LL-271: Exceptional Daily Profit - Strategy Validated

Date January 20, 2026

Category SUCCESS / S…

Today’s Numbers

What Count
Lessons Learned 6
Critical Issues 3
High Priority 2
Improvements 1

Tech Stack Behind the Lessons

Every lesson we learn is captured, analyzed, and stored by our AI infrastructure:

flowchart LR subgraph Learning["Learning Pipeline"] ERROR["Error/Insight
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

  1. No Lesson Lost: Every insight persists in our RAG corpus
  2. Contextual Recall: Before each trade, we query similar past situations
  3. Continuous Improvement: 200+ lessons shape every decision
  4. Transparent Journey: All learnings published publicly

Full Tech Stack Documentation

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 84/90 complete. 6 to go.