Artificial intelligence has moved fast, but trust has not kept pace. In this episode, Nam Nguyen, co-founder and COO of TruthSystems.ai, joins Greg Lambert and Marlene Gebauer to unpack what it means to build “trust infrastructure” for AI in law. Nguyen’s background is unusually cross-wired—linguistics, computer science, and applied AI research at Stanford Law—giving him a clear view of both the language and logic behind responsible machine reasoning. From his early work in Vietnam to collaborations at Stanford with Dr. Megan Ma, Nguyen has focused on a central question: who ensures that the systems shaping legal work remain safe, compliant, and accountable?

Nguyen explains that TruthSystems emerged from this question as a company focused on operationalizing trust, not theorizing about it. Rather than publishing white papers on AI ethics, his team builds the guardrails law firms need now. Their platform, Charter, acts as a governance layer that can monitor, restrict, and guide AI use across firm environments in real time. Whether a lawyer is drafting in ChatGPT, experimenting with CoCounsel, or testing Copilot, Charter helps firms enforce both client restrictions and internal policies before a breach or misstep occurs. It’s an attempt to turn trust from a static policy on a SharePoint site into a living, automated practice.

A core principle of Nguyen’s work is that AI should be both the subject and the infrastructure of governance. In other words, AI deserves oversight but is also uniquely suited to implement it. Because large language models excel at interpreting text and managing unstructured data, they can help detect compliance or ethical risks as they happen. TruthSystems’ vision is to make governance continuous and adaptive, embedding it directly into lawyers’ daily workflows. The aim is not to slow innovation, but to make it sustainable and auditable.

The conversation also tackles the myth of “hallucination-free” systems. Nguyen is candid about the limitations of retrieval-augmented generation, noting that both retrieval and generation introduce their own failure modes. He argues that most models have been trained to sound confident rather than be accurate, penalizing expressions of uncertainty. TruthSystems takes the opposite approach, favoring smaller, predictable models that reward contradiction-spotting and verification. His critique offers a reminder that speed and safety in AI rarely coexist by accident—they must be engineered together.

Finally, Nguyen discusses TruthSystems’ recent $4 million seed round, led by Gradient Ventures and Lightspeed, which will fund the expansion of their real-time visibility tools and firm partnerships. He envisions a future where firms treat governance not as red tape but as a differentiator, using data on AI use to assure clients and regulators alike. As he puts it, compliance will no longer be the blocker to innovation—it will be the proof of trust at scale.

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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

⁠⁠⁠⁠⁠Email: [email protected]
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript:

Few people understand the intersection of legal practice, data analytics, and diversity like Catherine Krow, Managing Director of Diversity and Impact Analytics at BigHand. In this episode of The Geek in Review, hosts Greg Lambert and Marlene Gebauer sit down with Krow to trace her journey from a high-powered trial lawyer to an influential legal tech leader. After seventeen years at firms like Orrick and Simpson Thacher, Krow’s turning point came when a client challenged her team’s billing after a major courtroom victory—a moment that sparked her mission to fix what she calls the “business of law.”

That single moment led to the creation of Digitory Legal, a company designed to give law firms the data and transparency they desperately needed but didn’t yet value. Krow describes how her framework—plan, measure, refine—became the basis for improving cost predictability and strengthening client trust. When BigHand acquired Digitory Legal in 2022, Krow’s vision found a larger stage. Now, her “data refinery” powers better pricing, resource allocation, and even equity within firms. As she explains, clean data doesn’t only improve profitability, it reveals hidden inequities in work allocation and helps firms retain their most promising talent.

Krow also digs into one of her favorite topics: “data debt.” Law firms are drowning in data but starved for information. She explains how poor data hygiene—like inconsistent time codes and messy narratives—has left firms unable to use their most valuable resource. BigHand’s impact analytics tools attack this problem head-on, transforming raw billing data into usable intelligence that drives decision-making across finance, staffing, and diversity efforts. And while the technology is powerful, Krow is clear that solving data debt is as much a cultural challenge as it is a technical one.

Another major theme is the evolving role of business professionals within law firms. Krow argues that lawyers’ traditional discomfort with financial forecasting and project management is holding firms back. Her solution? Combine legal expertise with the commercial acumen of allied professionals. Together, they can meet client demands for budgets, accountability, and measurable value—especially as AI begins to reshape how legal services are delivered and priced.

The episode closes with Krow’s broader reflection on the next decade of legal innovation. She warns that the biggest shift ahead isn’t about AI or analytics—it’s about mindset. Firms that embrace data-driven decision-making now will define the future of law; those that don’t will be left behind. Through her work at BigHand, Krow is helping to ensure that future is both more efficient and more equitable.

Links:

• Impact Analytics Software | BigHand
• Law Firms: Nail Pricing at the Buying Moment to Win Work and Safeguard Your Margins
• The Million Dollar Problem Law Firms Can No Longer Ignore
• BigHand 2025 Annual Legal Pricing and Budgeting Trends Analysis
• Navigating The Million Dollar Problem: Resource Management for Profitability, Client and Talent Retention

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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

⁠⁠⁠⁠⁠Email: [email protected]
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript:

This week we are joined by Anusia Gillespie, Enterprise Lead at vLex and debut novelist, as she shares her unique vantage point on the intersection of legal technology and the human side of law. Anusia traces her journey from commercial real estate finance attorney to global innovation leader, with roles at Harvard, UnitedLex, and Eversheds Sutherland, all driven by a mission to help lawyers by rethinking the systems they work in. Along the way she discovered that business-of-law blind spots, like a shocking embezzlement incident early in her career, revealed deeper structural issues that inspired her focus on system change.

Anusia describes how legal tech adoption often falters when lawyers’ reactions—especially negative ones—are misunderstood. Far from being a setback, she sees strong reactions as opportunities to engage skeptics and convert them into champions. She shares a vivid example from her current work at vLex, where an initially frustrated lateral partner became one of the firm’s most enthusiastic adopters after receiving attentive support and seeing immediate client impact. 

The conversation pivots to Anusia’s new novel Soul Toll, which blends contemporary and fantasy storytelling to examine the personal cost of high-performance legal culture. The book’s central metaphor, the “soul toll,” measures the tradeoff between meaningful work and draining obligations. Through her protagonist Ember, a high-achieving lawyer on a seemingly predestined path, Anusia explores how professional ambition can be engineered and how easy it is to let subtle daily tolls overwhelm the soul. Her goal is to give lawyers and other readers a practical framework for assessing that balance in their own lives.

As AI reshapes legal work, Anusia argues that lawyers need both the courage and the space to “fight for their light,” a phrase she uses as both a personal mantra and a rallying call in the novel. She emphasizes that the industry’s relentless pace will not slow down on its own, so lawyers and firm leaders must deliberately set boundaries and create pauses to prevent burnout. The discussion also explores how technology can relieve drudgery while prompting a new definition of professional competence that values human insight as much as efficiency.

Anusia closes with a challenge to law firm leaders: confront the mindsets shaped by the billable hour and empower lawyers to think beyond six-minute increments. From her perspective, real change begins in how lawyers structure their time and measure success. Whether she is leading enterprise strategy at vLex or writing visionary fiction, Anusia keeps a single purpose in view—helping lawyers build healthier, more sustainable careers. Listeners can find Soul Toll on Amazon and connect with Anusia on LinkedIn to continue the conversation.

Order Soul Toll today on Amazon

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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

⁠⁠⁠⁠⁠Email: [email protected]
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript:

Daniel Lewis joins us this week to trace a path from Ravel Law to LexisNexis to LegalOn, with a throughline of data-driven thinking and practical outcomes for lawyers. Stanford roots shaped early work on judicial analytics, then a front-row view inside a global publisher broadened focus to content, guidance, and the daily reality of in-house teams. That experience pointed straight at contract review as a top pain for corporate counsel, which led to LegalOn’s product mission and global push.

Data access still shapes progress. Case law digitization advanced through projects like Harvard’s archive, yet comprehensive coverage, secondary sources, and news remain guarded by incumbents. Daniel explains why large datasets give scale, why startups face steep hurdles, and why thoughtful product scope matters. The lesson, build where data, workflow, and user value intersect.

LegalOn’s hybrid approach blends large models with attorney-built playbooks, practice notes, and suggested clause language. Consistency matters more than clever one-offs, so reviews align to standards, not model whimsy. Daniel shares a memorable demo from a rival where a phantom “California Code section 17” alert appeared, a cautionary tale that underscores the need for guardrails, verification, and explainability.

Conversation turns to multi-step agents and matter management. Picture an intake email from sales, missing key fields. An agent requests what is needed, opens a matter, applies a tailored playbook, highlights non-negotiables and fallbacks, then keeps stakeholders informed as work progresses. LegalOn also converts existing playbooks and prior redlines into AI-ready guidance, reducing setup chores while preserving organizational risk preferences.

Finally, Daniel outlines new muscles for legal teams. Daily AI usage shifts time from line-by-line edits to judgment, negotiation strategy, and process leadership. Tech fluency, business orientation, and change leadership rise in importance, along with a steady diet of outside-legal analysis from voices like Ben Thompson and Benedict Evans. The message, free lawyers from sludge, raise the ceiling on strategic work, and build for long-term improvement across the legal function.

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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

⁠⁠⁠⁠⁠Email: [email protected]
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript:

This week, we talk with Gabe Pereyra, President and co-founder at Harvey, about his path from DeepMind and Google Brain to launching Harvey with Winston Weinberg; how a roommate’s real-world legal workflows met early GPT-4 access and OpenAI backing; why legal emerged as the right domain for large models; and how personal ties to the profession plus a desire to tackle big societal problems shaped a mission to apply advanced AI where language and law intersect.

Gabe’s core thesis lands hard, “the models are the product.” Rather than narrow tools for single tasks, Harvey opted for a broad assistant approach. Lawyers live in text and email, so dialog becomes the control surface, an “AI associate” supporting partners and teams. Early demos showed useful output across many tasks, which reinforced a generalist design, then productized connections into Outlook and Word, plus a no-code Workflow Builder.

Go-to-market strategy flipped the usual script. Instead of starting small, Harvey partnered early with Allen & Overy and leaders like David Wakeling. Large firms supplied layered review, which reduced risk from model errors and increased learning velocity. From there the build list grew, security and data privacy, dedicated capacity, links to firm systems, case law, DMS, data rooms, and eDiscovery. A matter workspace sits at the center. Adoption rises with surface area, with daily activity approaching seventy percent where four or more product surfaces see regular use. ROI work now includes analysis of write-offs and specialized workflows co-built with firms and clients, for example Orrick, A&O, and PwC.

Talent, training, and experience value come next. Firms worry about job paths, and Gabe does not duck that concern. Models handle complex work, which raises anxiety, yet also shortens learning curves. Harvey collaborates on curricula using past deals, plus partnerships with law schools. Return on experience shows up in recruiting, PwC reports stronger appeal among early-career talent, and quality-of-life gains matter. On litigation use cases, chronology builders require firm expertise and guardrails, with evaluation methods that mirror how senior associates review junior output. Frequent use builds a mental model for where errors tend to appear.

Partnerships round out the strategy. Research content from LexisNexis and Wolters Kluwer, work product in iManage and NetDocuments, CLM workflows via Ironclad, with plans for data rooms, eDiscovery, and billing. Vision extends to a complete matter management service, emails, documents, prior work, evaluation, billing links, and strict ethical walls, all organized by client-matter. Global requirements drive multi-region storage and controls, including Australia’s residency rules. The forward look centers on differentiation through customization, firms encode expertise into models, workflows, and agents, then deliver outcomes faster and at software margins. “The value sits in your people,” Gabe says, and firms that convert know-how into systems will lead the pack.

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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

⁠⁠⁠Email: [email protected]
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript

This week we sit down with Suzanne Konstance, Vice-President and General Manager for Legal and Regulatory US at Wolters Kluwer. She outlines how the company supports professionals in highly regulated fields with software and authoritative content. Operations span multiple countries with a deliberately local approach, where teams design solutions for each market. Listeners get a clear view of scope, from enterprise legal management to recent additions such as Brightflag, alongside deep subject expertise.

Konstance explains a core focus on regulatory compliance across securities, tax, IP, and employment. The aim is simple, help clients stay out of court. Continuous change drives editorial work, with authors and editors tracking shifts, executive orders, and practical effects. Provenance, version history, and context matter, supported by structured meta tagging which helps search and AI retrieve the right source every time.

In a segment on trust, the conversation moves to standards for accuracy and auditability. Clients tell Wolters Kluwer quality outranks speed for research, so the team emphasizes authoritative sources and transparent sourcing. Konstance walks through a recent non-exclusive content license with Harvey for primary law from US and German collections, part of a broader collaboration strategy which also includes VitalLaw AI and new cross-border features. The goal is a reliable workflow where answers cite sources, show currency, and fit real practice.

Real user labs reinforce these priorities. At AALL, librarians worked hands-on in a sandbox session with no guided prompts, pushing tools to limits and asking tough questions. One theme dominated, transparency, with live citations and source trails visible during use. Editors remain in the loop to curate likely questions, collect feedback, and refine outputs, while openness about progress helps teams separate market sizzle from dependable results.

Looking ahead, Konstance expects roles to shift toward managing agents and setting clear instructions, similar to supervising a room full of interns, with strong expertise still required for oversight. Teams will need to train newcomers on fundamentals, auditing, and controls, so technology serves professionals, not the reverse. She also shares sources she follows, industry conversations with customers, conferences, LinkedIn, X, plus guidance from a long-standing internal Center of Excellence for AI. For more on Wolters Kluwer initiatives, listeners can visit wolterskluwer.com and explore the Legal and Regulatory section along with the AI hub.

Also, check out Jerry David DeCicca and his new album, Cardiac Country.

Links:

• Wolters Kluwer Legal & Regulatory U.S. page
• Wolters Kluwer's AI center
• The press release announcing the content licensing agreement with Harvey
• VitalLaw

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: [email protected]
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript:

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: [email protected]
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript:

This week we are joined by Mirat Dave and Danish Butt of Swiftwater & Co. as they step into the studio to make a simple claim, investigations and legal operations should serve the business, not slow the business. Mirat traces a path across law, technology, and global risk, then explains why a team blending strategy with implementation drew him to Swiftwater. Danish shares a wry origin story from early e-discovery days and outlines Swiftwater’s north star, the seven C’s, connecting, caring, collaboration, creating, curiosity, courage, and confidence. The tone stays pragmatic, no hype, and a few laughs land along the way.

Global scope often triggers the “Germany is different” objection. Mirat acknowledges regional nuances, then reframes the discussion, most of the process is common across borders. The move that matters is standardization plus smart technology, including AI, to shift from linear headcount answers to scalable capacity. The payoff is speed, consistency, and lower risk. The team urges leaders to act like business owners, align processes to growth, margin, assets, and purpose, and resist the reflex to hire without redesigning the work.

Budget hurdles come next. Leaders struggle to win funds for process change or platforms, while headcount requests sail through. The fix is storytelling backed by math, present a structured plan, expected savings, and a clear ROI in the language a CFO or GC uses daily. Danish widens the lens on metrics, many teams still track counts and cycle times, while value measures like revenue protected or reputation preserved sit at the bottom of the list. The guidance is to flip that order, tie decisions to value, and approach AI as a set of pointed use cases with measurable outcomes, not a monolith.

Legal ops gets a moment in the spotlight as the quiet power. Danish reminds listeners that service functions exist to help the organization win, recognition matters, yet trust erodes when tools take center stage over results. Mirat presses the enablement mindset with a memorable image, legal, risk, and investigations are the pit crew, the business is the driver. Faster pits win races. He shares examples, a government contractor lifted renewal success by turning compliance visibility into proactive reminders and playbooks. In investigations, trend analysis by region, level, and timing surfaces fixes that reduce incoming allegations, lighten workloads, and raise quality.

The crystal ball stays practical. Danish advises teams to treat AI as a working style backed by a two-year plan, prepare data, pick targets, and avoid both freeze and frenzy. Mirat expects investigation platforms to evolve from reporting systems into work systems, triage, plan creation, interview guidance, and repeatable playbooks that lift speed and consistency.

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: [email protected]
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript:

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: [email protected]
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

In this episode of The Geek in Review, we welcome back Pablo Arredondo, VP of CoCounsel at Thomson Reuters, along with Joel Hron, the company’s CTO. The conversation centers on the recent release of ChatGPT-5 and the rise of “reasoning models” that go beyond traditional language models’ limitations. Pablo reflects on his years of tracking neural net progress in the legal field, from escaping “keyword prison” to the current ability of AI to handle complex, multi-step legal reasoning. He describes scenarios where entire litigation records could be processed to map out strategies for summary judgment motions, calling it a transformative step toward what he sees as “celestial legal products.”

Joel brings an engineering perspective, comparing the legal sector’s AI trajectory to the rapid advancements in AI developer tools. He notes that these tools have historically amplified the skills of top performers rather than leveling the playing field. Applied to law, he believes AI will free lawyers from rote work and allow them to focus on higher-value decisions and strategy. The discussion shifts to Deep Research, Thomson Reuters’ latest enhancement for CoCounsel, which leverages reasoning models in combination with domain-specific tools like KeyCite to follow “breadcrumb trails” through case law with greater accuracy and transparency.

The trio explores the growing importance of transparency and verification in AI-driven research. Joel explains how Deep Research provides real-time visibility into an AI’s reasoning path, highlights potentially hallucinated citations, and integrates verification tools to cross-check references against authoritative databases. Pablo adds historical and philosophical perspective, likening hallucinations to a tiger “going tiger,” stressing that while the risk cannot be eliminated, the technology already catches a significant number of human errors. Both agree that AI tools must be accompanied by human oversight and well-designed workflows to build trust in their output.

Looking to the future, Joel predicts that the adoption of AI agents will reshape organizational talent strategies, elevating the importance of those who excel at complex decision-making. Pablo proposes “ambient AI” as the next frontier—intelligent systems that unobtrusively monitor legal work, flagging potential issues instantly, much like a spellchecker. Both caution that certain legal tasks, especially in judicial opinion drafting, warrant careful consideration before fully integrating AI. The episode closes with practical insights on staying current, from following AI researchers on social platforms to reading technical blogs and academic papers, underscoring the need for informed engagement in this rapidly evolving space.

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: [email protected]
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

• Academic Papers:
  Weekly research for trends.
  scholar.google.com,
  ssrn.com,
  arxiv.org

• François Chollet: Balanced AI insights.
  x.com/fchollet
  fchollet.com
  
• Jason Wei (OpenAI): Reinforcement learning updates.
  x.com/jason_d_we
  openai.com/blog
• Geoffrey Hinton: AI research insights.
  x.com/geoffreyhinton
• Richard Sutton: Reinforcement learning and philosophical takes.
  incompleteideas.net
  Reinforcement Learning: An Introduction (Book):
  http://incompleteideas.net/book/RLbook2020.pdf
  Seminal work by Turing Award winner.
• University of Alberta Lab: https://rlai-lab.github.io
  Current research on scalable AI methods.

Blue Sky: ⁠⁠@geeklawblog.com⁠⁠ ⁠⁠@marlgeb⁠⁠
⁠⁠⁠⁠⁠Email: [email protected]
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript