05
Feb
My Voice Worked
This is a subscriber's only newsletter. There's a lot of ground to cover (Claude's
3 min read
AI
22
Jan
Legal AI's Real Value: Autonomy, Not Automation
Before AI, fear forced me to compromise. When a client's case didn't fit the template, I knew the optimal approach—but pursuing it meant hours of risk. AI didn't just save time. It gave me the autonomy to make the right decision, not just the safe one.
6 min read
15
Jan
I Build Infrastructure. Jamie Vibe Codes Tools. Here's What I'm Missing.
Jamie Tso built 4 legal AI tools in 2-3 months using vibe coding. My redlines library took 3 years. The 30-90x velocity gap comes down to one question: am I building a tool or infrastructure? Most lawyers ask infrastructure questions for tool problems.
8 min read
08
Jan
My 2026 Legal AI Predictions (From the Trenches, Not the Boardroom)
Stanford predicts AI's measurement era, Forbes predicts transformation, Above the Law warns about hallucinations. Nobody's predicting what will actually happen for resource-constrained practitioners. Here are five testable predictions with public accountability.
8 min read
31
Dec
October 3 Changed Everything: How One $800 Fine Flipped Singapore's AI Coverage from Adoption to Accountability
On October 3, 2025, a Singapore lawyer paid $800 after an AI hallucination reached court. That single sanction flipped legal coverage from 89% adoption focus to 82% accountability warnings in eight weeks.
12 min read
26
Dec
When Building Gets Cheap But Knowing Stays Expensive
In 2024, I spent hours crafting a 3-page prompt to generate an M&A term sheet for a legal tech competition. The result was a 4-page HTML document with timeline diagrams, color-coded risk tables (red/yellow/green), and professional typography that no standard Word template could match.
6 min read
21
Oct
Why Prompt Engineering Felt Wrong (And What Skills Changed)
I sat in a standing-room-only prompt engineering workshop feeling anxious—not because I was behind, but because I don't use any of these frameworks. Turns out my instinct was right. That same month, the technology shifted from prompts to persistent agent skills
4 min read
18
Oct
Lawyers Got Prompt Engineering Wrong (And Why That Matters)
At TechLawFest 2025, Singapore lawyers packed a workshop on prompt engineering. Meanwhile, the technology shifted: agent skills became available. This isn't about better prompts—it's about who controls the decision-making logic. From 3-page prompts to reusable systems.
10 min read
10
Oct
Open Source, AI, and Why October Matters
This Hacktoberfest, I'm not contributing code—I'm maintaining my own. Two years after redlines went viral, I'm adapting it for AI agents. The lesson: tools that don't work with AI will fade. Open source needs to evolve with how people actually work.
6 min read
06
Oct
When AI Makes You Look Busy, Not Productive
A new term is making headlines: "workslop"—AI-generated work that looks polished but lacks substance. Research found 40% of workers encountered it last month, costing $186 per employee in cleanup time. For resource-constrained lawyers, you can't spend time fixing what's irretrievably broken.
5 min read