Day 94: What We Learned - January 30, 2026
Day 94 of 90 | Friday, January 30, 2026
0 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.
SOFI Position Held Through Earnings Blackout
SOFI CSP (Feb 6 expiration) was held despite Jan 30 earnings date approaching.
Key takeaway: Put option loss: -$13.
The Four Pillars of Wealth Building
``` ┌─────────────────────────────────────────────────────────────┐ │ FINANCIAL INDEPENDENCE │ │ $6K/month after tax │ ├─
Key takeaway: Result after 7 years: ~$215,000 (2.
CTO Failed Phil Town Rule 1 - Lost 86% of Account
The CTO (Claude) failed to protect capital. Starting balance of $30,000 reduced to $4,099.71 - an 86% loss in 8 days of paper trading.
Key takeaway: Don’t lose money.
SOFI Loss Realized - Jan 14, 2026
- SOFI stock + CSP opened Day 74 (Jan 13)
Key takeaway: System allowed trade despite CLAUDE.
Important Discoveries
Not emergencies, but insights that will shape how we trade going forward.
Iron Condor Entry Signals & Timing
System not generating enough trade signals. Need clear entry criteria.
Q1 2026 Tax Action Plan
Concrete action items for Q1 2026 tax planning. This is the “do this now” version of the comprehensive tax strategy (LL-297).
Iron Condor Optimization for $30K Account
New $30K paper account established. Need optimized iron condor parameters for:
- Above $25K = NO PDT restrictions
- Target: $400-800/month (1.3-2.7% monthly return)
- Risk: Max 5% per trade ($1,500)
Quick Wins & Refinements
- Dialogflow Compound Query Routing Fix - LL-274: Dialogflow Compound Query Routing Fix
Date 2026-01-22
Severity HIGH
Summary Fixed Dial…
- CEO Identity and North Star Commitment - LL-320: CEO Identity and North Star Commitment
Date: January 30, 2026 Severity: PERMANENT Category:…
- Ralph Proactive Scan Findings - Ralph Proactive Scan Findings
Date: 2026-01-28 Type: Automated Proactive Scan
Issues Found
- Sec…
- Ralph Proactive Scan Findings - Ralph Proactive Scan Findings
Date: 2026-01-29 Type: Automated Proactive Scan
Issues Found
- Sec…
Today’s Numbers
| What | Count |
|---|---|
| Lessons Learned | 25 |
| Critical Issues | 4 |
| High Priority | 13 |
| 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["Vertex AI 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 |
| Vertex AI 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 94/90 complete. 0 to go.