Further Comments
Join legal technology experts Damien Riehl and Horace Wu as they explore the intersection of law and technology. In each episode, they discuss the latest trends, tools, and innovations shaping the future of legal practice, from litigation tech to transactional solutions.
Episodes
Two legal tech dudes meet outside and discuss rapid travel, conference buzz, and what we are hearing from law firms about AI.
Damien describes an Am Law 50 executive board preparing for agentic AI and considering a shift from billable hours to flat fees, while noting internal incentive and compensation conflicts.
We cover AI-native legal startups, how to begin adoption by mapping workflows, and concerns ab...
Horace and Damien record an unedited and unfiltered episode, opening with Horace’s stressful overnight apartment move in New York while planning a two-month summer trip to Australia.
We discuss legal tech execution versus announcements, discussing a link about Kirkland & Ellis’s reported $500 million AI commitment and whether it reflects real technology spend or largely lawyer hours, whi...
Damien Riehl and Horace Wu record a market catch-up episode covering AI hype and positioning in legal tech. They discuss in-house self-serve AI tools for business users and whether they implicate unauthorized practice of law. They examine what remains uniquely human for lawyers — trust, intuition, integrity — arguing each may erode as AI improves, while also giving examples of human lawyers’ counse...
Damien and Horace open season three of “Further Comments” with Lumio co-founders Ed Sohn (Chief Product Officer and general counsel) and Jae Um (Chief Growth Officer and head of knowledge). They discuss why legal AI sits on multiple, overlapping hype cycles and why market views diverge by buyer segment, work type, incentives, and user experience, creating fatigue and people “talking past each other...
LegalWeek Wrap: GenAI Valuations, Agentic Workflows, Build vs Buy, and the Future of Legal Work
Damien and Horace record an end-of-season-two LegalWeek conversation about how AI has shifted from flashy banners to an integrated reality, alongside soaring valuations for legal GenAI platforms Harvey ($11B) and Legora ($5.5B), which they contrast with the legal-content arms of Thomson Reuters, LexisNexis, and Wol...
In this episode of Further Comments, we discuss the latest developments in legal tech, AI, and the challenges and opportunities they present. From the impact of Claude's new legal plugin and the concept of vibe coding, to the evolving roles of lawyers and coders. We also explore the implications for access to justice and the need for reliable and useful AI tools in legal practice.
After a two month unplanned hiatus, in this episode, Damien and Horace wrap up 2025 discussing the latest trends in legal tech and AI.
From encoding morality to vibe coding by legal professionals, we cover recent developments that we should be watching. Along the way, we tackle the transformation in law firms towards AI adoption and debate the future of legal services in the context of accessible and open data....
In this episode of 'Further Comments', hosts Damien Riehl and Horace Wu chat with legal tech industry veteran Ken Crutchfield about navigating the future. The discussion revolves around the potential 'bubble' in legal technology and the impact of generative AI on the legal industry. The trio explores whether current trends mirror previous economic bubbles, the nuances of legal tech adoption amidst such uncertainties...
Join hosts Damien Riehl and Horace Wu on this episode of Further Comments as they welcome special guest Ted Theodoropoulos to discuss the recently concluded ILTACON 2025.
The trio delve into a variety of thought-provoking topics including the growing influence of large language models and AI on the legal industry, the prospect of non-lawyer ownership in law firms through alternative business structures (ABS), a...
In this episode of Further Comments, Damien and Horace are joined by Joe Green and Stephanie Goutos from Gunderson to discuss the integration of AI and technology in legal practice. The conversation covers Gunderson's innovative approaches, the adoption of tools like ChatGPT and Perplexity, and the challenges and opportunities in modernizing legal workflows. From humorous anecdotes to insights on future tech, this e...
Take a deep dive into the evolution of document management systems in law firms with hosts Damien Riehl and Horace Wu. Featuring expert insights from Mark Denner of Fireman & Co., this episode explores the history, current landscape, and future of DMS. Learn why systems like iManage and NetDocuments dominate the market, how AI could be poised to revolutionize DMS, and the unique challenges and innovations in the...
In this riveting episode of 'Further Comments', hosts Damien Riehl and Horace Wu welcome Dr. Megan Ma from Stanford to delve into the intersection of AI and legal practice. They discuss Megan's work on multi-agent simulations for training young attorneys, the significance of personas in AI models, and the future of AI in legal professions.
This episode offers a wealth of knowledge on how cutting-edge AI researc...
In this episode of Further Comments, hosts Damien and Horace dive into the state of knowledge management (KM) in the legal industry, discussing why traditional KM practices fall short and how artificial intelligence (AI) can revolutionize the field. Horace shares insights from interviews with KM leaders and discusses the implications of AI innovations like large language models on the future of legal practice. The e...
Join hosts Damien and Horace in their deep dive into the current state and future of AI in the legal sector.
They tackle three major topics: (1) the hype cycle of AI in tech, (2) the using autonomous agentsin legal practices, and (3) the feasibility of achieving Artificial General Intelligence (AGI).
Whether you're a legal professional, tech enthusiast, or just curious about the intersection of AI and law,...
In this episode of Further Comments, Horace and Damien is joined by Nick Abrahams from Norton Rose Fulbright. Nick shares his unconventional career journey, from working in a big law firm in Sydney, studying at USC Film School, to becoming a Hollywood studio executive and then a technology lawyer in Australia. The discussion explores what it takes to be a successful lawyer, the unique perspective gained from varied ...
Join Damien Riehl and Horace as they kick off Season 2 with an in-depth discussion about the intersection of Big Tech and Big Law.
They explore the recent news of Freshfields partnering with Google for generative AI, the potential of AI to disrupt legal services, and the impacts of large language models on the industry. They also delve into the future of law firms, the evolving role of legal tech companies, and...
In the finale episode of season 1, Damien Riehl and Horace Wu delve deep into the impact of large language models, agents, and the rapidly evolving landscape of legal tech.
Recorded live from a New York City park, they discuss their experiences from Legalweek, the future of legal startups, the role of VCs, and how AI is transforming workflows. Explore themes like knowledge management, the integration of proprie...
In this episode of 'Further Comments,' hosts Damien and Horace welcome Helder Santos from Bird and Bird to discuss the firm's decision to roll out the Gen AI platform, Legora.
They explore the pilot process, decision-making factors, and the blend of technology with traditional law practices. Helder shares insights into the cooperation between startups and established legal entities, the challenges and successes...
In this episode of Further Comments, hosts Damien and Horace are joined by Ben Chiriboga from Nexl to discuss how to effectively sell to lawyers in the age of artificial intelligence. They explore the dynamics of the crowded legal tech market, the role of storytelling in sales, and how Nexl’s CRM solution addresses the unique needs of law firms. The conversation delves into the complexities of relationship int...
In this episode of Further Comments, we are joined by the 'Duchess of Document Automation', Catherine Bamford. Catherine shares her journey and expertise in legal tech, particularly in document automation. We dive into the nuances of document automation, discussing the adoption cycles within law firms, the importance of continuous improvement, and the challenges and solutions brought by large language models (LLMs)....
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