Augustin Chan — AI Systems Engineer & Founder

Augustin Chan is the CTO and founder of Digital Rain Technologies. His work sits at the intersection of AI and culture, grounded in an enterprise architecture background. He also builds surgical software — small, high-leverage tools built to solve exactly one problem well.

Previously, Augustin served as Development Architect at Informatica, leading enterprise architecture for Fortune 500 customers across APAC, MENA, and Europe. Before that, he was a Senior Consultant at Dun & Bradstreet.

Augustin holds a B.S. in Cognitive Science with Specialization in Computation from UC San Diego.

Latest
What Claude Code Does Before the Model Sees Your Message
A deep dive into Claude Code's preprocessing pipeline — the 6-stage system that transforms raw user input into a carefully orchestrated message stream with context injection, file pre-reading, skill discovery, and message normalization. Based on source code analysis.Apr 2026

Essays

Short posts

Full archive

Building

  • Crawlopen-source
    Migration intelligence — automated discovery, risk scoring, and planning for legacy system modernization
  • ARA Evalopen-source
    Open-source framework for decomposing autonomous AI risk into 7 dimensions. Used by practitioners and enterprises to evaluate whether agents can act without human approval.
  • 8-Bit Oracle
    The I-Ching through the lens of retro computing and science fiction — tech-noir art and commentaries. Presented at Taipei Blockchain Week.
  • Six Lines
    iOS app for learning the I-Ching as literature and philosophy — bilingual hexagram reference with classical commentary and public domain masterwork art
  • QDayAnon Research Platform
  • Plum Blossom Computer (Consensus HK 2026)
  • seeded-iching-engine (GitHub)

Speaking

Consulting

People App, Travelbox