In this episode, I'm talking with Zack Shapiro, founder of an AI-native law firm, Rains LLP. Zack is a corporate lawyer focused on startups and business law who has transformed his two-person practice into a high-leverage powerhouse serving over 200 clients. Despite describing himself as "uniquely bad at using tech tools," he has pioneered a "Claude-native" workflow that uses agentic AI to handle his legal work.
We talk about the shift from "billable hours" to "high-judgment lawyering" and how prompting is becoming the most critical white-collar skill of the next decade. You’ll hear perspectives on why most legal tech "wrappers" are actually counterproductive that most lawyers are missing.
The Power of "Bare Metal": Why Zack avoids expensive legal AI platforms in favor of direct, "bare metal" interaction with reasoning models like Claude.
Prompting as an Essay: Moving beyond simple queries to 2,000-word "context dumps" that capture the nuance of a client's specific leverage and goals.
Building Custom "Skills": How to use your own past work as a reinforcement learning environment to create agentic workflows that compound in value over time.
The Entrepreneurial Opportunity: Why now is the greatest time in history for small, AI-empowered legal teams to steal market share from rigid, legacy firms.
The Hallucination Filter: Practical strategies for using AI to check itself, ensuring that "turning your brain off" never becomes an option.
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Each week I take what I'm hearing in conversations with legal leaders.
I analyze the market and track emerging trends in this AI era.
In my newsletter called The Future Lawyer Market Intel for the AI era
I'm focused on:
What AI is exposing
The opportunities
The blind spots
And the shifts shaping the next five years.
This is how you see the chessboard before everyone else does:
https://hollycope.my.canva.site/thefuturelawyer
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