Connecting Legal Education and Technology at a Tech Show

This week, we welcome back Kara Peterson and Rich DiBona of Descrybe to talk about the company’s rapid growth and its expanding role in legal research. Since their last appearance, Descrybe has not only built out new tools but also entered academia by joining the curriculum of more than 350 universities around the world. Kara reflects on her earlier career in legal education and how this new partnership feels like coming full circle. Together, she and Rich share how Descrybe is positioning itself to fill the gap left by other providers while keeping affordability and accessibility at the core of their mission.

A major highlight of the discussion is Descrybe’s unique approach to legal citators. Unlike traditional tools that often provide a blunt “treatment” of a case, Descrybe’s citator allows issue-level analysis and even introduces a “backwards citator.” This means researchers can see not only how later courts interpreted a case but also how the judges who wrote the opinion cited and treated earlier authorities. Rich explains the technical challenges involved in training their system on 30 million citations, while Kara describes how these innovations give researchers new storytelling and analytical power when building arguments.

The conversation also dives into the Legal Research Toolkit, Descrybe’s paid tier that offers a collection of tools designed for professionals who need more advanced case law analysis. While the company continues to provide free access to its core research platform, the toolkit adds features such as issue explorers and advanced citator functions. Kara emphasizes the company’s deliberately simple pricing model, which prioritizes trust and accessibility. At just $10 a month for non-commercial use and $20 for commercial users, the service is priced more like everyday software than the traditional high-cost legal research platforms.

The discussion moves into broader industry trends, including the wave of acquisitions by major players like Thomson Reuters and Clio. Kara and Rich note that while consolidation is reshaping the market, it also leaves space for new entrants to innovate. With data becoming the most valuable commodity in legal tech, Descrybe is building curated and clean datasets across statutes, regulations, state constitutions, and even attorney general opinions. Both guests highlight the importance of accuracy, data hygiene, and minimizing hallucinations, explaining how their closed-system approach helps ensure that results remain grounded in actual legal documents rather than speculative AI outputs.

Finally, the episode touches on ethics, recognition, and the future. Descrybe recently won the Anthem Award for Ethical AI, a nod to its safeguards against hallucinations and commitment to transparent data practices. At ILTACon, the team found themselves impressing not only potential clients but also leaders from larger companies who were curious about how such a lean startup was able to achieve so much. Looking ahead, Kara predicts the pace of change in legal technology will only accelerate, challenging law firms to keep up, while Rich warns of the commoditization of AI capabilities and stresses the importance of staying ahead of the curve. Together, they bring both humor and insight, reminding listeners that the legal research market is shifting quickly and that affordability, accuracy, and ethics will shape its next chapter.

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[Special Thanks to ⁠Legal Technology Hub⁠ for their sponsoring this episode.]

Blue Sky: ⁠⁠@geeklawblog.com⁠⁠ ⁠⁠@marlgeb⁠⁠
⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.com
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠