AI in law

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This week on The Geek in Review, Greg Lambert and Marlene Gebauer sit down to compare notes from a busy conference season. Marlene shares her experience at the American Legal Technology Awards where The Geek in Review was honored for excellence in journalism. She recounts the surreal joy of being recognized among friends and peers in legal tech, including fellow nominees like Steve Embry, and how a spontaneous speech turned out to be one of the night’s highlights. The duo reflects on how events like this underscore the sense of community that continues to define the innovation side of the legal industry.

Greg takes listeners behind the scenes at ClioCon, describing it as one of the most energetic user conferences around. He dives into his conversation with Clio CEO Jack Newton and how the company’s recent vLex acquisition signals a bold expansion into the Big Law space. With $900 million in funding, Clio appears ready to bridge the divide between small-firm technology and enterprise-level workflows. Greg also teases an illuminating hallway chat with Ed Walters, now at Clio Library (formerly vLex/Fastcase), about the major leap forward in legal research accuracy driven by improvements in RAG (retrieval-augmented generation) and vector database indexing.

Marlene offers her own takeaways from the Association of Corporate Counsel (ACC) Annual Meeting, where AI and governance dominated the agenda. She describes a landscape where in-house lawyers are wrestling with both the promise and peril of generative AI, from shadow AI concerns to data hygiene challenges. Her biggest surprise was seeing law firms themselves exhibiting at the ACC conference, signaling a shift toward direct engagement between firms and their corporate clients in shared learning spaces.

Together, Greg and Marlene unpack the emerging themes of human-centered governance, the evolving role of AI in matter management, and the race among vendors to automate core workflows without losing the human touch. From Clio’s plans to build AI-driven workflow mapping that could auto-draft documents, to Marlene’s caution about how bespoke law firm processes might resist one-size-fits-all automation, their discussion paints a picture of a profession both accelerating and self-checking at once.

The episode winds down with lighter reflections on travel mishaps, conference after-parties, and the long arc of Richard Susskind’s The End of Lawyers? conversation—still ongoing, now infused with cautious optimism about AI’s role in expanding access to justice. As always, they end where The Geek in Review thrives: at the intersection of humor, humility, and the hopeful chaos of legal innovation.

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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

⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.com
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript:

Continue Reading Conferences, Catch-ups, and Clio’s Big Swing at Big Law

This week we are joined by Patrick DiDomenico and Kevin Klein, two longtime builders of knowledge programs and legal tech gatherings. They walk through the evolution of KM&I for Legal, now entering year three, and the debut of its co-located counterpart, Legal Tech Connect. Both events run in New York on October 22 and 23, with a single community, two distinct agendas, and one big goal, stronger conversations across buyers, builders, and backers of legal tech.

Patrick traces the roots, from the ARK KM era to the launch of KM\&I, then to twisting Kevin’s arm to join as a producer. A larger home opened the door to ambitious programming, Ease Hospitality at 3rd and 40th near Grand Central. Think bright rooms, live plants, strong AV, plenty of seating, and an adjacent tenant lounge with coffee, terrace, and breakout nooks. Lessons from last year show up in smart touches, an overflow room streaming the main stage for those who need to handle calls or email without missing core content, longer breaks for real conversations, and, yes, food worthy of repeat trips.

Format matters here. KM&I holds firm on peer-to-peer sessions led by law firm professionals. Providers participate through tight five-minute spotlights between talks, plus optional demo rooms during generous coffee breaks and lunch. Legal Tech Connect flips the lens, product stories on stage, founder journeys, market forces, and regulatory themes. A crossover ticket lets attendees roam freely between both programs. Breakouts return by popular demand, a C-suite roundtable, KM 101 for newcomers, a track for KM attorneys and PSLs, and a managers and directors forum that grew from attendee feedback.

Themes thread across both days. ROI from AI and KM tools appears throughout, from data strategy as a differentiator to co-development case studies. Expect a lively take on the rise of the legal engineer, with skills for scaling tools and driving adoption, plus a frank discussion about where these roles sit inside firms. Professor Michele DiStefano opens with client centricity, drawing on her research and book, with every attendee receiving a copy. She then moderates a session at Legal Tech Connect on how legal tech companies sell to law firms, bridging provider goals with buyer needs. Another panel stages the AI conversation among a partner, pricing director, client, and innovation lead, a timely look at value, billing, and collaboration.

The bigger story is community. Patrick and Kevin highlight the peer network that forms in hallways and over coffee, mentors found by chance, and ideas that travel home in workable form. Legal Tech Connect brings investors and founders into the mix, which raises the quality of dialogue on funding, product focus, and adoption. Looking ahead, they predict fewer conferences, higher quality bars, and a shift toward substance over appearance. Listeners who want more details, including registration, should visit kmniforlegal.com and legaltechconnect.com. The two events sit side by side in October, and the goal is simple, leave with practical ideas, new contacts, and a clearer view of where legal innovation heads next.

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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

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

Transcript:

Continue Reading KM&I Meets Legal Tech Connect: Two Tracks, One Community with Patrick DiDomenico and Kevin Klein

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.

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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

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

Transcript:

Continue Reading The Cytator Strikes Back: Kara Peterson & Rich DiBona On Descrybe’s Fresh Take on Legal Research