Eugene Oleinik

Founder in Residence at Antler. Former CTO of 12Go, APAC’s leading ground transportation OTA, where I spent 10 years scaling the platform to 30,000 bookings daily with a remote team of 50 engineers.

Based in Singapore. Building what’s next.

Projects: fnkey · feeder · ai-9p

Web 4.0 Is Open Databases

I asked my AI agent to plan a family escape from Chiang Mai’s burning season. It reverse-engineered a proprietary air quality encoding, scraped flights, checked fuel costs, and compared 15 cities across 10 years of data. This is what Web 4.0 actually looks like: open databases + agents that query them.

March 29, 2026 · 7 min · Eugene Oleinik

Agent Experience (AX): 10 Principles for CLI Tools AI Agents Can Actually Use

We have UX. We have DX. But AI agents are now the primary users of developer tools, and nobody’s designing for them. Here are 10 principles from watching real agent behavior through usage telemetry.

February 27, 2026 · 5 min · Eugene Oleinik

How We Make Claude Remember: Learnings Over Skills

Skills don’t reliably auto-invoke. We built a three-layer system: searchable learnings files, a curation skill, and a post-commit hook that reminds you to document.

February 2, 2026 · 2 min · Eugene Oleinik

Serve Markdown to AI Agents (10x Smaller Payloads)

An entire infrastructure layer (CSS, JS, frameworks) is becoming optional for a growing class of consumers. Here’s how to serve markdown via HTTP content negotiation.

February 2, 2026 · 2 min · Eugene Oleinik

The AI Data Trap: Why You Can't Opt Out

Your competitor uses Claude or GPT to move faster. If you don’t, you fall behind. That’s the trap.

January 28, 2026 · 1 min · Eugene Oleinik

The Best Agent Architecture Is Already in Your Terminal

The Best Agent Architecture Is Already in Your Terminal My project’s CLAUDE.md file had grown to 55KB—242 learnings crammed into one massive file. The problem? Claude prepends this file to every single prompt. A 55KB context file means less room for thinking and acting. Sessions hit context limits faster. Compaction happens sooner. I noticed the degradation: sessions became noticeably shorter, context compaction triggered more frequently, and the agent seemed to lose track of longer conversations. ...

January 12, 2026 · 3 min · Eugene Oleinik

Zero-Friction Database Branching with Neon, Git Hooks, and Claude Code

Zero-Friction Database Branching with Neon, Git Hooks, and Claude Code I’ve been refining my Neon database branching setup over the past few months. Here’s the current state: fully automated branch lifecycle with zero manual cleanup. The Goal When I git checkout -b feat/x: Neon database branch created automatically .env.local updated with the new connection string Vercel preview deployment uses the same isolated database When I merge and delete the branch: ...

January 7, 2026 · 4 min · Eugene Oleinik

The Iteration Trap: When AI Makes You a Spectator

The iteration trap is really a clarity trap. You iterate because you don’t know what you want.

December 28, 2025 · 3 min · Eugene Oleinik

Adding LLM Polish to a Speech-to-Text App

How I added an optional LLM post-processing step to clean up voice transcriptions, with lessons on prompt engineering and graceful degradation.

December 22, 2025 · 5 min · Eugene Oleinik

Building an AI-Powered Changelog GitHub Action

How a 87-line inline script became a reusable GitHub Action for AI-generated changelog summaries posted to Slack.

December 22, 2025 · 5 min · Eugene Oleinik