The WeWork Lawyer Who's Coming for Big Law

Hi friends,

Fifteen years ago, when I was building WeWork Labs with Matt and Adam, one of the first people to believe in our vision was Jen Berrent. She came on board as our first sponsor. In the years that followed, Jen helped transform WeWork from a nascent idea into a category-defining platform.

Now, after watching Jen navigate one of the most complex legal landscapes in startup history as WeWork's general counsel and president, I'm thrilled to be backing the next chapter of her career. Flybridge led a $4M seed round in Covenant, an AI-native law firm.

The Big Law Disruption

When pension funds, endowments, and sovereign wealth funds invest in private markets, they still pay law firms eye-watering fees to review limited partner agreements and side letters. The prestige supposedly justifies the price. After all, bigger firms have seen more deals, right?

But what if AI could deliver better insights at 10% of the cost?

Covenant's tools use large language models to parse fund documents, flag issues, and suggest stronger terms tailored to each investor's playbook. It’s like TurboTax for fund docs. Suddenly, the old way looks absurdly overpriced.

By The Numbers

• 48 signed clients as of June 30, including endowments, foundations, pension plans, and sovereign wealth funds

• 50% average monthly client growth in 2025

• Monthly transaction volume up 50% since January

Law Firm 2.0

Covenant is part of the “Law Firm 2.0" movement, tech companies with legal services layered on top. As Jen puts it: "Uber didn't sell software to taxi companies." They redefined how people think about getting from A to B.

While companies like Harvey and Ironclad sell tools to law firms, Covenant is selling directly to the clients who typically hire Big Law. It's counsel-as-a-service.

Our Thesis

At Flybridge, we look for three things in AI investments. Efficiency (10X productivity gains), expansion (unlocking new markets), and excitement (rapid adoption). Covenant hits all three.

Hot Links

🏛️ WeWork's former top lawyer is building an 'AI-native' law firm - Melia Russell at Business Insider dives deep into Covenant's story and how they're reimagining legal services for the AI age.

🚀 NetBox Labs Raises $35M Series B - Another Flybridge portfolio company crushing it. NetBox has become the global standard for infrastructure management, trusted by AI data centers, Fortune 500s, and government agencies.

🧠 Memory: The Missing Piece for Real Intelligence - Flybridge’s Daniel Porras Reyes explores why memory systems might be the real moat in AI. As context windows expand to millions of tokens, the ability to remember and learn over time becomes the killer feature.

If you're an institutional investor still paying Big Law rates for fund document review, we should talk. If you're building something that makes expensive professional services look outdated, I want to hear from you.

Until next time,

Jesse