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In this episode of The Geek in Review, hosts Marlene Gebauer and Greg Lambert sit down with Otto von Zastrow, the founder and CEO of MidPage.AI, an AI-native legal research platform. With a recent $4 million seed round and an ambitious mission to rival legacy research tools, MidPage is drawing attention across the legal industry. Otto shares his unconventional journey from AI-powered lawn robotics to transforming how litigators interact with case law. His pivot into legal tech was fueled by a combination of technical curiosity, the rise of language models, and firsthand insight from his lawyer friends overwhelmed by inefficient research workflows.

Otto walks listeners through the core of MidPage’s offering, which includes the usual suspects—case law, statutes, regulations—but with a twist: smarter search tools, intuitive UI, and features like a proprietary citator and their newly launched Proposition Search. This feature aims to solve the long-standing “needle-in-a-haystack” problem by surfacing judicial language that matches precise arguments, accompanied by contextual metadata and filters. Otto highlights that the goal isn’t just to match or mimic tools like Lexis or Westlaw, but to rethink what legal research should feel like when modern AI capabilities are built in from the ground up.

One of the more unique aspects of MidPage’s product development is their internal “kangaroo court”—a monthly teamwide challenge where employees, regardless of role, must conduct legal research using MidPage or traditional tools. Otto notes that this process not only improves product design but builds real empathy for the user experience. Engineers and designers are encouraged to think like litigators, helping identify pain points and close functionality gaps. As a result, the product continually evolves based on firsthand user scenarios, not just speculation.

The episode also delves into the data-side challenges that have historically prevented innovation in legal research. Otto explains why now—thanks to improved AI models and open access to data—is a rare inflection point for startups. He emphasizes the strategic importance of MidPage building its own case law dataset to avoid being beholden to incumbents. This independence allows them to innovate more freely, enhance precision, and lay the groundwork for broader API access that could empower the next generation of legal tech tools.

Finally, the conversation looks ahead. Otto predicts that AI will amplify the capabilities of individual lawyers, enabling them to process more data at greater depth. In a world where clients are increasingly self-educating with tools like ChatGPT, MidPage aims to provide lawyers with the means to maintain credibility and efficiency while ensuring accuracy. As AI models grow more capable and agentic, Otto sees an evolution not just in how legal research is conducted, but in how lawyers interact with knowledge, data, and ultimately their clients.

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 Otto von Zastrow on MidPage.AI and the Future of AI-Powered Legal Research

In this special episode of The Geek in Review, we take the new ChatGPT Advanced Voice Mode for a spin, inviting it to analyze and discuss all 23 episodes from the podcast’s 2025 season. The episode kicks off with a high-level overview of the biggest legal tech themes from the year so far. ChatGPT Voice quickly identifies a significant shift toward agentic AI tools—those that go beyond automation to become integrated partners in the legal workflow. These tools are helping firms reimagine service delivery, improve access to justice, and rethink the very structure of their businesses.

Throughout the episode, the trio explores consistent trends shared by legal tech leaders in recent episodes. These include the integration of AI into core legal tasks, such as contract review and litigation support; the rise of new business models like value-based pricing; and the ongoing focus on ethical AI use. Specific guests like Feargus MacDaeid and Nnamdi Emelifeonwu (Definely), Atena Reihani (ContractPodAI), and Raghu Ramanathan (Thomson Reuters) are spotlighted for their insights into embedding AI directly into lawyers’ existing toolsets to streamline and elevate legal workflows.

The conversation then turns to the importance of human oversight in maintaining trust and legality as AI becomes more embedded in legal systems. ChatGPT Voice references Garfield AI’s regulated model and various RAG-based solutions to illustrate how combining AI efficiency with human judgment creates responsible innovation. The emergence of AI-native law firms and more flexible pricing models reflects an industry on the cusp of transformation, driven by both technological advancement and client-centered thinking.

Marlene and Greg also take a moment to reflect on the human stories behind the tech. They highlight episodes featuring guests like Laura Clayton McDonald, Kenzo Toshima, Wendy Jepsen, and Gabriela Izturiz, who bring servant leadership, change management, behavioral science, and personal purpose into their work. These conversations remind us that innovation in legal tech is as much about people and values as it is about platforms and code.

To close out the episode, the hosts pose their signature “crystal ball” question. ChatGPT predicts the legal tech breakthrough of 2025 will be the mainstream adoption of agentic AI systems that proactively support legal professionals in real time. It also shares that its favorite episode was the one featuring Garfield AI and their bold vision of a fully AI-powered law firm handling small claims—a true glimpse of the future. Whether you’re curious about cutting-edge workflows or inspired by legal professionals integrating their personal passions into practice, this episode captures a compelling snapshot of where legal tech is headed.

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 What Does ChatGPT Think of Our 2025 Episodes? We Ask ‘Her’

In this episode of The Geek in Review, we welcome Feargus MacDaeid and Nnamdi Emelifeonwu, co-founders of Definely, to discuss how their shared experiences as practicing lawyers shaped a groundbreaking accessibility solution for contract review. Feargus, who is visually impaired, and Nnamdi, his former colleague at Freshfields, describe how their friendship and professional collaboration led to a tool designed not only for those with disabilities but for all attorneys grappling with voluminous transactional documents. Listeners learn that Definely began as a way to help Feargus navigate complex contracts more efficiently, and through iterative prototyping, evolved into a productivity suite that addresses universal pain points in the pre-execution stages of contract life cycles.

Feargus explains that his journey to co-founding Definely began with personal necessity: having gone blind from a degenerative condition by his early twenties, he pivoted from a computer science career at Microsoft to law school, relying on assistive technology and immense personal support. Once at Allen & Overy, the limitations of existing tools became starkly apparent—searching for defined terms meant losing one’s place in a 300-page agreement and juggling layers of nested definitions by reading aloud via text-to-speech. The cognitive load was immense. By collaborating with Nnamdi, who recognized that if a solution could serve Feargus, it would benefit everyone, they embraced the principle of “designing for the edge”—creating a platform that brought definitions, clauses, and cross-references into context without interrupting a lawyer’s focus.

Nnamdi takes listeners on a tour of Definely’s three core components: Vault, Draft, and Proof. Vault functions as a dynamic repository for templates, clauses, and precedent documents, enabling users to pull in the most relevant resources from connected document management systems. Draft keeps the user anchored in the current clause while instantly displaying any linked provisions or schedules in a sidebar, eliminating the need to scroll, split screens, or flip between pages. Proof automates common pre-signing checks—verifying cross-references, punctuation, and legal grammar—to ensure a polished final draft. Together, these tools exemplify how Definely streamlines contract creation by surfacing precisely the needed information in a lawyer’s line of sight, thereby maintaining context and reducing manual navigation.

The conversation shifts to quantifying Definely’s impact on law firms. Nnamdi cites a study indicating that attorneys save up to 45 minutes per day—roughly a 90 percent reduction in time spent on tedious tasks—by using Definely’s context-aware navigation. Beyond hard metrics, the founders emphasize “soft benefits” such as reduced cognitive fatigue, higher morale, and improved client value. To capture these less tangible gains, Definely’s customer success team works closely with firms to customize usage dashboards and collect feedback. Feargus and Nnamdi also reflect on the broader legal tech landscape, noting that firms are experimenting with in-house development, acquisitions, and partnerships. They believe collaboration between vendors and firms will ultimately prevail, as specialized expertise in areas like machine learning ops and user experience is hard to cultivate internally and essential for maintaining cutting-edge tools.

Finally, the episode zeroes in on technical and operational safeguards to ensure accuracy and maintain the “human in the loop.” Feargus describes how Definely uses a retrieval-augmented generation (RAG) approach, chunking and embedding each contract so that any language model query is strictly grounded in the document’s own text. By setting the model’s temperature to zero and building guardrails at every step, they contain hallucinations and ensure that the attorney remains the arbiter of correctness. Looking ahead, both founders predict a rise in agentic workflows—small, task-specific language models that plug into a suite of specialized tools—and a greater emphasis on UX design as software shifts from simple point-and-click interactions to more dynamic agent-driven processes. As the hosts close the interview, Definely’s mission emerges clearly: empower lawyers to work smarter by bringing critical contract information into focus, while preserving the essential human judgment at the core of legal practice.

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 Designing for the Edge: Feargus MacDaeid and Nnamdi Emelifeonwu on Definely’s AI-Powered Contract Navigation

On this episode of The Geek in Review, we welcome Philip Young, co-founder and CEO of Garfield AI, the first AI-powered law firm approved for practice by the UK’s Solicitors Regulation Authority (SRA). The episode kicks off with a discussion of recent stories that explore AI’s evolving role in legal proceedings, such as avatars testifying in court and the ethical challenges that arise when deepfakes and synthetic personas enter the legal process. Philip, a seasoned litigator and technologist, draws from his 25 years of legal experience to weigh in on the potential and perils of AI-driven courtrooms, emphasizing the importance of authenticity and trust in legal proceedings.

Young shares the backstory behind Garfield AI, which was inspired by a real-world problem faced by his brother-in-law, a plumber who struggled to recover small debts from non-paying clients. Seeing an opportunity to help small businesses navigate the small claims process efficiently, affordably, and with minimal friction, Philip set out to build a system that mirrors what a traditional law firm would do—without the high cost or time burden. Garfield reads invoices and contracts, verifies the legitimacy of claims, guides users through pre-action letters, claim filings, and even court preparation, all while remaining compliant with UK legal standards.

One of the most unique features of Garfield AI is its dual design: it serves both pro se claimants and can be white-labeled for use by traditional law firms. Young explains how legal professionals can integrate Garfield into their workflows, using it to generate documents under their own branding while Garfield handles the backend. This hybrid approach provides flexibility for users, whether they prefer a self-service platform or seek a human-in-the-loop experience. Garfield’s early success has sparked interest across the legal spectrum—from solo practitioners to regulatory bodies—demonstrating that AI can support, rather than displace, the legal profession.

The conversation also delves into Garfield’s journey to regulatory approval. Young describes the rigorous process of working with the SRA, ensuring the platform aligned with legal duties to clients and the courts. He highlights the importance of maintaining accountability and explains how Garfield was rolled out cautiously, with layers of human oversight and a roadmap toward data-driven, risk-based review. With increasing inquiries from international regulators and courts, Young sees the platform as a potential blueprint for improving access to justice beyond the UK, although he notes that success depends on a supportive regulatory environment, judicial openness, and sufficient technological infrastructure.

Beyond the tech, the episode emphasizes the human element of law. Young passionately advocates for AI as a tool that enhances legal practice rather than replaces it—freeing lawyers from mundane tasks and enabling them to focus on strategy, advocacy, and client care. He shares his hope that Garfield AI and similar innovations will close the access-to-justice gap by enabling small-value claims to be pursued cost-effectively and fairly. As he notes, AI may never replace the human lawyer’s emotional intelligence and presence in court, but it can certainly help more people get there.

To learn more about Garfield AI and its innovative approach to legal automation, listeners can visit www.garfield.law. This episode is a must-listen for anyone interested in the intersection of law, technology, and the future of justice. As always, the podcast ends on a warm note with music by Jerry David DeCicca, underscoring a thought-provoking conversation that blends legal tradition with the tech of tomorrow.

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 Philip Young of Garfield AI: The World’s First AI Law Firm Gets the Green Light

This week, we welcome Laura Clayton McDonnell, President of the Corporates Business Segment at Thomson Reuters. Laura shares her inspiring journey from corporate securities law to executive leadership at top technology companies, including Apple, Cisco, IBM, Microsoft, and now Thomson Reuters. She discusses how her Silicon Valley upbringing and her family’s immigrant experience have shaped her leadership style and commitment to innovation in the legal industry. Laura’s personal purpose—rooted in values like courage, curiosity, and integrity—drives her mission to deliver measurable value to clients through legal technology and business transformation.

The conversation highlights the rapid advancements in legal technology, with a special focus on the impact of generative AI and agentic AI in the legal sector. Laura explains how she stays ahead of legal tech trends by collaborating with internal teams, listening to customer feedback, and learning from her daughter, a practicing transactional lawyer. She emphasizes the importance of a growth mindset, continuous learning, and adaptability—qualities she honed during her time at Microsoft under Satya Nadella’s leadership and through the teachings of Carol Dweck’s “Growth Mindset.”

Laura provides insights into how corporate legal, tax, and compliance departments are evolving from traditional cost centers to strategic business partners, thanks to innovative legal technology solutions from Thomson Reuters. She discusses how tools like Westlaw, Practical Law, Legal Tracker, and OneSource are helping legal professionals automate routine tasks, reduce contract review times by over 80%, and save millions on outside counsel spend. Laura notes that forward-thinking clients are not just adopting new legal tech tools—they are developing comprehensive strategies to transform business processes, training, and staffing for the future of legal work.

The episode also explores the rise of alternative legal service providers (ALSPs) and the ongoing bifurcation of the legal market driven by technology adoption. Laura observes that general counsel are increasingly sophisticated in their approach, weighing cost, complexity, and the use of AI to achieve better outcomes. She stresses that legal technology is now essential for law firms and ALSPs alike, and that innovation and value delivery are key to staying competitive in the evolving legal landscape.

Looking to the future, Laura predicts that predictive analytics, risk assessment, and cross-functional insights will become even more critical for legal, tax, and compliance professionals. She highlights the growing demand for skilled legal talent and the importance of ongoing training, ethical oversight, and building resilient, growth-oriented teams. Laura encourages legal industry leaders to prepare for a future where human expertise and advanced legal technology work together to drive strategic transformation and business success.

For more information on legal technology trends, AI in the legal industry, and upcoming events, Laura invites listeners to connect with her on LinkedIn or visit Thomson Reuters. She also highlights the upcoming Thomson Reuters customer conference in November, where attendees can experience product demos and gain insights into the latest legal innovation and industry trends.

 Links:

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 Laura Clayton McDonnell on Legal Technology, AI, and Corporate Transformation at Thomson Reuters

This week, we sit down with Kenzo Tsushima, Managing Director of Mind Factory at Morae, to discuss how AI is transforming legal operations and consulting services. Kenzo shares his unique career journey, blending a passion for technology with legal expertise, and highlights why the legal industry is positioned to leverage AI advancements more quickly than heavily regulated sectors like healthcare. With a background that spans consulting leadership and GC roles, Kenzo offers a rare dual perspective on how law firms and corporate legal departments can future-proof themselves by embracing emerging technologies like MorAI, Morae’s proprietary AI platform.

Kenzo discusses the creation of MorAI, launched in mid-2023, as a response to widespread legal tech “decision fatigue” — where an abundance of AI tools overwhelms buyers. Rather than pushing generic solutions, Morae designed MorAI around highly specific legal workflows such as contract review, RFP response automation, and internal helpdesk queries. Kenzo emphasizes the importance of “solutionizing” AI: showing real, targeted results rather than relying on hype. Using examples like their Helpdesk module, Kenzo explains how legal teams can instantly boost efficiency by querying historical RFP responses and deploying AI for natural language document reviews, significantly reducing administrative burdens across legal and procurement functions.

A strong advocate for servant leadership and human-centric AI adoption, Kenzo outlines how Morae’s approach goes beyond technology — focusing heavily on change management and upskilling legal professionals. Through programs like SEEDS (Skill Enablement Employee Development Series), Morae invests in developing both consulting and technology skills among its team. Kenzo notes that traditional legal professionals, often unfamiliar with public speaking or technology tools, can thrive when given structured, bite-sized learning opportunities. This consultative-first mindset, he argues, not only improves client outcomes but creates a more resilient and engaged workforce.

Addressing cybersecurity and data privacy concerns, Kenzo details Morae’s use of private Azure instances and multiple legally trained LLMs to ensure client data security and confidentiality. Unlike public AI tools, MorAI is designed to be a trusted legal companion that never co-mingles client data or trains on external internet content. Kenzo also explains why Morae’s strategy of multi-LLM deployment (leveraging OpenAI, Anthropic, and others) future-proofs clients against rapid developments in AI models — ensuring their legal technology stacks remain agile and powerful over time.

Finally, Kenzo shares his insights on the challenges ahead for the legal industry: decision fatigue, resistance to change, and the crucial need to align with younger generations’ expectations around technology use. He urges law firms and corporate legal departments to rethink build-vs-buy strategies, embrace commercially available solutions, and foster AI champions within their organizations. As new roles like legal engineers and prompt engineers emerge, firms that support AI-enabled upskilling and servant leadership will not just survive — they will lead the next era of legal innovation.

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 Kenzo Tsushima of Morae on Innovation, Change Management, and Servant Leadership

This week we welcome Raghu Ramanathan, President of Legal Professionals at Thomson Reuters, for an insightful discussion on the profound impact of Artificial Intelligence (AI) on the legal industry. Bringing a fresh perspective shaped by his extensive background in technology leadership at companies like SAP and strategy consulting with McKinsey, Raghu shares why he believes the legal sector, alongside healthcare, stands at the forefront of the AI revolution. His journey into the legal tech world, driven by the transformative potential of AI, sets the stage for a deep dive into current trends, future predictions, and the strategic initiatives shaping the future of law.

Central to the conversation is Raghu’s updated perspective on the evolution of law firms, revisiting predictions he first made in 2017. He outlines a compelling framework describing “three waves” of AI adoption currently underway. The first wave, “Optimization,” which many firms are experiencing now, focuses on using AI to enhance existing workflows, making tasks faster and more efficient. The second wave, “Re-engineering,” involves fundamentally rethinking processes, staffing models (including the traditional pyramid structure), pricing strategies, and the very nature of legal work to leverage AI’s capabilities more deeply. Looking further ahead, the third wave anticipates the emergence of entirely “New Business Models,” where law firms might offer tech-based services, explore adjacent business lines, embrace true outcome-based pricing, and potentially even reshape the legal value chain.

The discussion delves into the significant implications these waves have for law firm talent and structure. Raghu predicts a shift in the traditional law firm pyramid, potentially leading to leaner associate ranks but a greater need for experienced partners and, crucially, integrated tech talent. This necessitates not only attracting technologists but also potentially rethinking firm equity structures to retain them. Furthermore, the skill set required for the “lawyer of the future” is evolving; proficiency in delegation to AI tools, broader unstructured problem-solving, and embracing technological integration will become paramount, demanding changes in legal education and professional development.

Thomson Reuters is actively navigating and shaping this transformation, particularly through its AI platform, CoCounsel. Raghu highlights the rapid evolution of CoCounsel, emphasizing the continuous development of new “skills”—capabilities ranging from summarization and research to drafting and complex analysis like the innovative “Claims Explorer.” He explains TR’s strategy involves integrating proprietary data (like Westlaw), client-provided documents, and public information, leveraging advancements in Large Language Models (LLMs) from various providers to deliver comprehensive and powerful AI assistance. Prioritizing new skill development involves balancing significant client value with technical feasibility, constantly informed by close collaboration with innovation-focused customers.

Beyond law firms, the conversation explores the crucial role and adoption of AI within the court system. Raghu notes a surprising enthusiasm among courts, driven by the urgent need to address growing case backlogs and enhance access to justice within tight budgets. He points to Thomson Reuters’ significant partnerships, including a major agreement to deploy AI tools across the US federal courts and ongoing collaboration with the National Center for State Courts (NCSC), which is fostering education and policy discussions among judges and court staff nationwide. Complementing product innovation, TR’s expanded “Customer Success” initiative underscores the importance of user adoption, providing dedicated resources and best practices to help lawyers and legal professionals effectively integrate AI tools into their daily workflows, ensuring technology translates into tangible value.

Concluding with a look ahead, Raghu anticipates that smaller and mid-sized law firms may initially leverage AI more aggressively as a competitive equalizer, pushing larger firms to make bolder, more strategic moves beyond simple optimization. He stresses that the ultimate differentiator for success in the AI era will likely be less about the technology itself and more about effective change management—strategic clarity, operational implementation, and fostering a culture that embraces new ways of working. The rapid pace of AI adoption already witnessed in the legal sector signals that this transformation is not a distant prospect but a present reality reshaping the industry at an unprecedented speed.

Read the Whitepaper: “2025 Generative AI in Professional Services Report“

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 Charting the Three Waves of Legal AI Transformation with Thomson Reuters’ Raghu Ramanathan

This week, we sit down with Sam Flynn, COO and co-founder of Josef, to separate substance from hype in the rapidly evolving world of legal tech. Sam shares his passionate stance that “RAG is not dead,” defending Retrieval-Augmented Generation (RAG) as a foundational and still deeply relevant method for deploying AI in the legal industry—despite the flashy allure of agentic AI. His nuanced take reminds listeners that success in this space depends not only on the sophistication of the technology, but on doing the “boring” foundational work: ensuring data integrity, context-aware chunking, and responsible workflows.

Throughout the discussion, Sam champions the idea that great legal technology should not just enhance expert workflows but make legal information accessible to non-experts. With examples from Josef’s clients like L’Oréal, Bumble, and Bupa, Sam illustrates how Josef’s tools allow legal departments to offload routine work through reliable self-service systems—freeing up time for more strategic thinking while improving speed, compliance, and consistency across organizations. He makes the case that empowering end users with trustworthy tools isn’t just good tech—it’s a new model for scaling legal and compliance services.

A key highlight is Josef’s Roxanne project, developed in collaboration with Housing Court Answers and NYU. Roxanne is an AI-powered tool designed to help tenants in New York navigate the complexities of housing law. Sam outlines the safeguards that ensure Roxanne’s answers are accurate and compliant, such as closed-domain data sources, human-in-the-loop validation, and smart escalation workflows. The conversation touches on the broader access to justice (A2J) implications of this technology—arguing that when designed carefully, AI can amplify the reach and impact of legal aid organizations by orders of magnitude.

The episode doesn’t shy away from the tensions legal professionals feel when automation enters their domain. Sam offers a powerful reframing: instead of seeing these tools as a threat, lawyers should view them as opportunities to offload low-value tasks and expand their influence. The goal, he says, is not to cut jobs—but to redefine the kind of work legal professionals do, making space for more proactive, strategic, and meaningful engagements within organizations and communities.

As the conversation wraps, Sam shares his optimism about the future—tempered by a clear-eyed understanding of the human factors that will determine success. While the technology is ready, the question is whether legal professionals will step up and take the lead. His call to action is clear: focus less on the hype, and more on the systems, safety, and trust that make tech transformative. Whether you’re a legal technologist, innovator, or cautious observer, this episode offers a grounded and inspiring look at what it takes to build legal tech that actually works.

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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

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

Transcript

Continue Reading RAG is Not Dead: Josef’s Sam Flynn on Legal Tech That Works

This week we sit down with Sean West—co-founder of Hence Technologies and author of Unruly: Fighting Back When Politics and Law Upend the Rules of Business. Together, they explore the shifting fault lines where law, technology, and geopolitics collide. From the growing reliance on generative AI in legal work to the erosion of rule of law and the emerging threats (and opportunities) facing knowledge workers, Sean offers a strikingly global—and at times unsettling—view of the legal profession’s next frontier.

The conversation kicks off with a discussion on the Law360 survey showing that 62% of lawyers are using ChatGPT in some aspect of their work. Sean explains the popularity of general-purpose AI tools over legal-specific ones as a matter of price, accessibility, and perceived innovation. While lawyers trust themselves to edit AI outputs, Sean warns that this passive use of AI could slowly and invisibly displace traditional legal roles, without firms consciously realizing what’s been lost.

The discussion deepens as Sean introduces the idea of passive job displacement—where tasks once assigned to junior lawyers, interns, or external vendors are quietly absorbed by AI tools. He likens it to carrying “a quarter of a human brain in your pocket” for $20 a month. What starts as convenience becomes infrastructure, and over time, demand for human input declines. He also questions the long-term viability of legal tech products that can’t clearly outperform generalist AIs like ChatGPT or Claude.

Sean then draws on his geopolitical expertise to underscore the urgent need for situational awareness in law firms and businesses alike. He explains how political volatility—from China and Taiwan to Europe’s regulatory tactics—can suddenly reshape the legal landscape. Rather than relying on traditional prediction models or complex advisory plans that get shelved, Sean emphasizes proactive legal scenario planning. His new product, Hence Global, offers a “geo-legal” lens on global news, customized for specific legal practice areas to help firms act instead of react.

We push further into the implications of “front-stabbing” politics, where once-hidden power plays are now openly transactional. Sean describes a world where AI-driven lobbying, mass arbitration spam, and “robot lawyers” can reshape public policy or flood companies with legal claims at scale. He argues that when the rules are ambiguous, large players will push boundaries—and smaller players may get squeezed out. In a world without a clear referee, the game favors those who can afford better tools and faster moves.

Finally, Sean challenges legal and corporate leaders to stop avoiding the hard conversations. Whether embracing AI to boost productivity or choosing to protect jobs, organizations must be transparent. “Let’s front-stab about it,” he says. Make your commitments public—whether you’re retraining your workforce or doubling down on AI-driven efficiency. Because in a world where legal, political, and technological lines blur, silence isn’t just unhelpful—it’s a risk.

Links and Mentions:

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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

Transcript

Continue Reading Front-Stabbing the Future: AI, Law, and the Global Unraveling of Rules with Sean West