Day 78 of 90 | Wednesday, January 14, 2026

Answer Block

Answer Block: 12 days remaining in our journey to build a profitable AI trading system.

12 days remaining in our journey to build a profitable AI trading system.

Every mistake is a lesson in disguise. Today we uncovered a critical flaw in our system - the kind that separates amateur traders from professionals who survive long-term.


The Hard Lessons

These are the moments that test us. Critical issues that demanded immediate attention.

SOFI Ticker Blackout Violation

Trading workflow was configured to execute credit spreads and CSPs on SOFI, despite CLAUDE.md explicitly stating SOFI was on blackout until Feb 1 (earnings Jan 30, IV 55%).

Key takeaway: PR

Important Discoveries

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

Mandate Violation - Manual Work Handoff

CTO violated CLAUDE.md mandate: “Never tell CEO to do manual work - If I can do it, I MUST do it myself”

CTO Autonomous SOFI Exit Decision

  • Feb 6 expiration is AFTER Jan 30 earnings

Missing OptionsPosition Class Broke CI Tests

CI workflow “Run All Tests” failed with:

Quick Wins & Refinements

  • January 14, 2026 Loss Root Cause Analysis - On January 14, 2026, the paper trading account suffered a $65.58 daily loss when the system correctl…
  • CTO Directive Violations - Crisis Level - In a single conversation, the CTO (Claude) violated multiple core directives:…
  • Resource Evaluation: Systems Thinking Audiobook - - Title: System and Systems Thinking – Fundamental Theory and Practice
  • Author: A. Gharakha…
  • SOFI Earnings Risk - Emergency Close - Short puts on SOFI (strike $24, exp Feb 6) held through earnings date (Jan 30)….

Today’s Numbers

What Count
Lessons Learned 12
Critical Issues 1
High Priority 4
Improvements 7

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 78/90 complete. 12 to go.


*Related: Complete Guide to AI Iron Condor Trading Our North Star Strategy*