Zach talks with Jen Berrent, former WeWork executive and founder of Covenant, an AI-first law firm reimagining how deals get done. They dive deep into what it means to build a law firm from the ground up around artificial intelligence — not as a tool, but as the foundation. Jen shares her perspective on why too much work still runs through Big Law, how AI is transforming the middle tier of legal work, and what it takes to balance human expertise with machine efficiency.

In this episode:

What an “AI-first” law firm actually looks like

How Covenant is redesigning legal workflows from scratch

The problem with Big Law’s “too much work, too few alternatives” model

Why reading comprehension is AI’s legal superpower

Building client trust in the age of automation

How AI can accelerate deals — without sacrificing rigor

The difference between a “relationship ramp” and a “SaaS snowball”

The challenges (and advantages) of raising funding in legal AI

Lessons from Robin AI’s struggles — and why clarity of business model matters

Why this is a once-in-a-generation moment for lawyers who want to innovate

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