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