Jake Heller (Co-founder & CEO of Casetext)

In this episode of the Slow Hunch, I spoke with Jake Heller, co-founder and CEO of Casetext, a legal tech startup that pioneered the use of large language models in the legal industry.

Jake and his co-founders built Casetext over a decade —  going through multiple pivots before eventually finding PMF as an AI tool that helped lawyers do better and faster legal research. In 2023, Casetext was acquired by Thomson Reuters for $650 million. 

In this conversation, Jake recounted how an early relationship with the research team at OpenAI got them access to GPT-4 (before the launch of ChatGPT!) and how they decided to hard pivot over the course of just two weeks. 

As a former lawyer himself, Jake has a unique take on the challenges of building and selling cutting-edge software in an industry that has traditionally been a late adopter of tech. 

This was a really fun conversation (you can probably tell because it’s longer than our usual episodes). 

Hope you enjoy! 

Chapters 

• 00:00:00 Cold open
• 00:06:15 How Jake found himself in legal tech
• 00:10:07 Building Casetext
• 00:28:41 Getting early access to GPT-4 
• 00:38:21 The AI pivot 
• 00:46:38 Convincing the team
• 00:57:03 Engineering solutions to improve real-world performance 
• 01:07:06 Jake’s thoughts on the future of the legal industry
• 01:14:29 Closing thoughts

What is The Slow Hunch?

The Slow Hunch explores how big ideas form over long periods of time. Big innovations are often characterised as single “eureka” moments, when in fact they're often the culmination of many smaller ideas coalescing over a long period of time. On this podcast, USV's Nick Grossman explores how those ideas took shape, and the nonlinear paths of the people behind them.