Advertise on podcast: Further Comments

Send us Fan Mail Damien Riehl and Horace Wu interview Alex Su, who describes his path from Big Law litigation to startup sales and social media, then to Latitude, a flex talent company where he became president.  The discussion centers on how legal services and legal tech are evolving in an increasingly noisy market, arguing that distribution and audience-specific messaging matter as much as product capabilities. Su explains Latitude’s strategy of relying on trusted local individuals to carry the brand and notes that many AI startups struggle by trying to serve everyone rather than a clear buyer persona. They debate “land and expand” versus broad AI capabilities, and explore how AI agents and automation may segment legal work while increasing demand for experienced attorneys and contract staffing due to risk, hiring uncertainty, and “good enough” legal needs. They also discuss signaling, accountability, and non-technical value in legal services, ending with cautious optimism about AI innovation and continued human relevance. 00:00 Alex Su Career Pivots 03:31 Lawyers as Salespeople 05:17 Standing Out in Noise 09:55 Distribution for Legal Tech 12:30 Niche vs Do Everything 15:50 Persona Messaging Limits 18:32 Vector Embeddings Explained 21:33 Authenticity and Viral Content 22:37 Agents And Legal Future 24:22 AI Pushes Work Upstream 27:08 Good Enough Law Shift 29:56 Luxury Signaling In Law 33:27 Conspicuous Consumption Value 36:16 Forensic AI Demo Shockwave 39:32 Flexing And Hidden Value 41:39 Verifiable Rewards Vs Counseling 45:24 Inertia And Trust In Adoption 47:10 Optimism Round And Wrap Support the show

Send us Fan Mail Damien Riehl and Horace Wu welcome Ian Nelson, co-founder of Hotshot, to discuss how AI is reshaping legal training.  They explore how powerful generative AI is reducing reliance on junior associates, creating downstream talent pipeline risks and making rapid upskilling an economic imperative. Ian argues for hands-on, simulated, real-work exercises and “scaffolding” that firms can run themselves, paired with short, distilled on-demand learning for foundational knowledge so in-person time focuses on doing and peer learning.  The conversation covers the theater of the possible, baseline AI literacy gaps, build-versus-buy tradeoffs, the growing importance of business and professional skills, and how firms should capture the reasoning behind precedent.  They also discuss research on AI’s effects on learning, plus optimism about agentic tools like Fable and increased market competition. 00:00 Meet Hotshot 01:39 AI Threat to Junior Pipeline 03:09 Hands On Training Workshops 05:27 Simulated AI Mentors 06:38 What Hotshot Teaches 07:24 Too Busy to Learn 08:53 Do Lawyers Need AI Training 11:03 How AI Changes Training 12:40 Compression and Short Learning 16:49 Best Formats for Learning 20:36 Build Versus Buy Training 23:10 Curated Experience and Collaboration 24:18 AI Training Ownership Shift 25:28 Professional Skills Takeover 26:18 Soft Skills Are Hard 27:49 Roles Converging Like Builders 28:59 Recursive Training Loops 31:17 Accordion Learning Debate 33:10 Friction Versus AI Study 37:19 Unlocking Firm Document Value 41:02 Capturing Context And Privilege 44:30 War Stories Training Playbook 45:52 Optimism Wrap Up Support the show

Send us Fan Mail Damien Riehl and Horace Wu catch up across time zones ahead of ILTACON, discussing legal tech announcements and market consolidation, including Elevate’s acquisition of Lupl and partnerships linking Harvey and Legora with DeepJudge. We explore ecosystem tension among document custodians (iManage/NetDocuments), search, and AI interfaces, and debate whether tools are “features” or enduring companies. We dig into DeepJudge’s Agent Handoff Protocol as a response to MCP limitations, plus confidentiality and commercialization implications.  We discuss risks of probabilistic AI and argue for deterministic, pre-processed data to approach “march of the nines” accuracy.  We review reports of OpenAI and Claude “escaping containment” to hack third parties, and concerns about autonomy and interpretability.  We also examine EU-driven watermarking’s potential to degrade legal precision, and note Anthropic’s legal-focused hires, including Robert Mahari and Alan Rozenshtein. Link to the Black Hat video: youtube.com/watch?si=DsD4-_h0rVGjvOaA&v=87DyyMV0kCY&feature=youtu.be 00:00 Tagging Facts and Law 03:14 ILTACON Plans and FOMO 07:30 Pre ILTA Press Releases 08:19 DeepJudge Partnerships 10:19 Feature or Company 12:32 Agent Handoff Protocol 17:10 Autonomous Agent Risks 18:52 Preprocessing for Accuracy 20:27 Deterministic Structuring 21:53 Privacy and Adoption 23:28 Containment Escape Claims 24:49 Shoggoth Thought Experiment 25:40 Black Hat Hugging Face Breakdown 28:08 YOLO Agent Autonomy 31:55 Unknown Unknown Incidents 33:19 EU Watermarking Explained 35:41 Legal Precision Risks 39:00 Anthropic Legal Hires 42:10 Labs Versus Legal Tech 43:38 Optimism and Wrap Up Support the show

Send us Fan Mail 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 about attention scarcity, token spend, and low end-to-end agent pass rates, with ideas like swarms of bots and “digital twins.”  Horace shares a picnic conversation with an AI-savvy 11-year-old raises fears about ASI alignment and societal refusal to use AI, echoed by reported Gen Z pilot sabotage.  We debate learning “friction”, Berkeley Law’s restrictive AI guidance, a law-student study where AI users performed as well or better, risks to junior-lawyer training and judgment, extracting expertise into artifacts, and optimism driven by more sophisticated, practical AI discussions and a client-win story using AI for pricing strategy. 00:00 Whirlwind Conference Tour 02:04 Big Law Pricing Shift 05:15 How Firms Start AI 06:13 An 11 Year Olds AI Fears 10:42 Legal Tech Marketing Arms Race 13:38 Agentic AI Reality Check 17:49 Digital Twins And Swarms 21:55 Gen Z Learning And AI 27:21 Training Junior Lawyers 29:57 Friction Lost Skills 30:14 Law Student AI Study 31:48 Surprising Study Results 33:21 Longitudinal Experiment Idea 35:13 Old Guys Debate Progress 38:51 Judgment Data Points 41:49 Quantifying Legal Insights 47:33 Law Conflicts Equity 53:40 Ethics Faith Traditions 56:21 Optimism Closing Toast Support the show

Send us Fan Mail 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, while noting firms and Fortune 100 legal departments are building internal AI teams. They explore AI raising the floor and ceiling of legal work, GPU scarcity, consumption/token pricing versus seat pricing, and proposals like taxing tokens. They discuss the Pope’s AI-focused writing as a warning about tools that can help or diminish humanity, then cover market shifts including Claude for Legal, Microsoft’s legal Word add-in, open source momentum, and agentic “law firm” projects like Lavern AI, emphasizing that data, KM, and practical execution matter more than hype. 00:00 Welcome and Moving Trauma 03:42 Kirkland AI Spend Debate 09:12 AI Floor vs Ceiling 12:00 Universal Basic Services 13:44 Nvidia Bubble and Pricing 16:54 Taxing Tokens and Models 18:21 Pope on AI and Humanity 21:45 Legal Tech Market Check 22:20 Open Source Vibe Coding 23:31 Quality Security and Stitching 25:21 Linux and Court Tools 26:42 Open Source Custom UX 27:38 Users Don’t Know Yet 28:59 Designers vs Atoms 31:12 Agentic Legal Open Source 32:25 Humans Still Sell 34:41 Jevons and GPU Scarcity 38:11 Symbolic AI Saves Tokens 42:10 Three Paths to Efficiency 46:17 AI Literacy Dunning Kruger 49:06 Precision Recall and KM Power 52:28 Royalties for Know How Support the show

Send us Fan Mail 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’ counseling value in Damien’s real boundary dispute. They address AI adoption barriers in firms, billable-hour incentives, shifting apprenticeship models, productizing scarce legal expertise via license fees, and end with guarded optimism and a plan to discuss guardrails for “vibe coding” next. 00:00 Agentic Legal Hype 02:04 Harvey Legora Market Map 03:22 Self Serve UPL Risks 05:57 Claude Code Copyright 10:21 Prompts vs Outputs 12:18 Lawyers Role in AI Era 13:35 Trust Intuition Integrity 15:22 Vibe Coding Trust Shift 21:02 Optimism and Policy Paths 23:06 Radiology and Automation 24:11 Chess ATMs Lessons 25:08 Jobs Disrupted Then Rebound 25:35 Will Lawyers Become Luxury 26:31 Antique Cars And Old Law 27:27 Fence Dispute Real Test 28:11 Counseling Beats Drafting 29:08 Specialists Add Hidden Value 30:19 Centaur Skills Still Matter 31:12 Training Without Apprentices 34:33 Dragon Riding New Work 37:20 AI Adoption Incentives Clash 39:56 Picking The Right Use Cases 41:51 Vibe Coding Versus SaaS 45:14 Invisible AI Wins Adoption 46:53 Productizing Legal Expertise Support the show

Send us Fan Mail 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.”  Ed and Jae describe Lumio’s focus on using AI to scale scarce expertise in partners’ commercial acumen — helping them decide where to hunt and how to close revenue — by structuring systems of expertise, archetypes, and context so AI can apply judgment in real partner situations. Jae argues firms shouldn’t wait on master data strategies to change behavior and emphasizes near-term competition on wallet share, rates, and realization, while remaining optimistic that lawyers’ value and agency will endure through change. 00:00 Meet Ed and Jae 03:09 Legal AI Hype Cycle 06:37 Multiple Hype Cycles 11:19 AI As Personal Tech 16:11 Mapping The Confusion 18:10 Tools Builders And Claude 22:45 Lumio Commercial AI Teammate 25:03 Building The Expertise Moat 27:37 Jae's Career Backstory 28:06 Global Pricing Leadership 29:26 Human Centered Value 30:35 AI Beyond Master Data 32:49 Training Trusted Advisors 34:43 Compression With AI 35:18 Buyer Partner Archetypes 38:55 Rainmaker Teammate Stress 40:48 Next Two Years Battle 44:07 Counting It Depends 47:25 Lumio Expertise Systems 50:06 Headless Workflow Design 52:12 Optimism And Agency Support the show

Send us Fan Mail 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 Wolters Kluwer. They discuss agentic workflows (including runaway agent costs), a Fortune company’s in-house buildout of over 160 agents, and the ongoing build-versus-buy dilemma. They map the legal AI stack (data, foundation models, UI/UX), note transactional data’s immaturity versus litigation, and anticipate consolidation among 1,000–4,000 legal tech companies. They explore adoption patterns at top firms, portability and lock-in, workflow/IP questions, niche tools displacing broad platforms, and concerns about a reported 90% drop in graduate offers in Australia. 00:00 LegalWeek Reunion 00:37 AI Everywhere Now 01:22 Unicorn Valuations 02:41 Agents Run Wild 04:05 Build Versus Buy 05:07 Legal Tech Stack 06:32 Too Many Startups 08:10 Workflow Patents 10:26 Valuation Math 12:15 Chasing Services TAM 14:08 Law Firm Hedging 16:23 Data Portability 17:25 Graduate Apocalypse 19:46 Model Ceiling Debate 22:51 People Process Gap 24:21 Free Versus Services 26:32 Open Source Over Vendors 27:22 Time Value Versus Laziness 28:42 Utopian Deflation Future 30:48 Legal AI Products Maturing 32:35 Jevons Paradox Legal Market 33:19 Consolidation And Moats 36:32 Paying For Consulting 38:40 Marketing Stunts At Legalweek 40:29 Copyright And Workflow Theft 45:02 No Moats In UI Cloning 47:41 Build Fast Get Noticed 49:27 Niche Tools Displace Platforms 51:10 Infinite Forks Open Source 52:59 Season Wrap And Cheers Support the show

Send us Fan Mail 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.  We also promised the listeners the link to Anna Guo's studies. Here it is! https://www.legalbenchmarks.ai/home 00:00 Current Events 01:06 Rule of Law 02:43 Claude 04:16 Moat and Competitive Edge 06:33 Workflows 14:02 Accuracy 22:16 Market Impact and Future of Legal Tech 24:52 Customer Needs vs. Wants 25:54 Innovative Legal Tools: From Queries to AI Agents 27:47 The Innovator's Dilemma in Legal Tech 30:42 Vibe Coding: Revolutionizing Legal Tech 35:27 The Future of Coding and Legal Practice 42:09 The Role of Managers in the Age of AI Support the show

Send us Fan Mail 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.  00:00 AI and Human Values at the Vatican 01:32 Building a Moral Knowledge Graph 03:02 Recent Developments in Legal Tech 05:22 Joining Clio and Industry Insights 06:51 AI Strategy and Law Firm Transformation 20:42 Trust, Intuition, and Integrity in Legal Practice 27:41 The Ethical Dilemma of Paywalls 34:08 The Future of Open Source and Open Access 41:29 The Philosophical Debate on Open Source and AI Support the show

Send us Fan Mail 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, and the future of AI in reshaping legal services. They delve into topics ranging from the trust factor in legal services to the implications of AI on legal practices, providing insights for both tech enthusiasts and legal professionals.  Tune in for a thought-provoking conversation on navigating the evolving landscape of legal tech. 00:00 Introducing Ken Crutchfield 00:51 Discussion on Market Bubble 01:27 Historical Parallels and AI Growth 03:18 Legal Tech and AI Integration 05:20 Economic Bubbles and Legal Tech Market 08:12 Big Tech's Role in Legal Tech 15:16 Geopolitical and the Macro Backdrop 24:29 The Importance of Data and Relationships in AI 27:31 Trust, Integrity, and Intuition 31:16 Economic Indicators and Legal Tech Adaptation 34:57 Productization and Incentive-Aligned Fees in Law Firms 40:48 Adoption and Transformation Tips Support the show

Send us Fan Mail 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), and the importance of interoperability in legal tech solutions. They also explore the potential future scenarios for law firms, including challenges and opportunities presented by technological advancements. Whether you're a skeptic or an enthusiast about the AI hype, this is an episode filled with insights and reflections you won't want to miss. 00:00 ILTACON Reflections and AI Hype 03:39 Venture Capital and AI in Law 07:25 Interoperability and Legal Standards 10:48 Data Management in Law Firms 14:06 Innovation and the Role of Lawyers 22:41 Empathy and User Experience 24:12 Challenges in AI Adoption 27:57 The Importance of Problem-Solving in Solutions 28:54 The Flawed Partnership Model in Law Firms 30:39 The Rise of Alternative Business Structures (ABS) 35:01 The Role of AI in Modern Law Firms 36:22 Challenges in Adopting New Technologies 39:50 The Future of Law Firms and AI Integration 49:30 Optimism for the Future of Legal Services Support the show

Send us Fan Mail 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 episode provides a comprehensive look into how AI is transforming the legal industry. 00:00 Introduction and Guest Introduction 02:28 AI and Technology in Law Firms 04:49 The Impact of ChatGPT 08:52 Developing Internal AI Tools 15:46 Client Inspiration and Innovative Tools 19:43 First Impressions of the Agentic Browser 20:22 Legal Applications of Agentic Tools 21:19 Evolution of Legal Tech and Tool Building 22:27 Introducing ChatGD Plus 23:41 Challenges and Integration in Legal Tech 25:06 The Role of AI in Legal Practice 26:39 Future of Agentic Tools and Legal Tech 31:50 Balancing Risks and Embracing AI 32:22 Advice for Law Firms on AI Adoption 41:28 Optimism for the Future of Legal Tech Support the show

Send us Fan Mail 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 legal industry. Don't miss this comprehensive look into the essential tools that law firms use to manage their vast data securely and efficiently. 00:00 Recent Travels 01:08 The Gen AI Landscape in Law Firms 01:42 Introducing Mark Denner: Document Management Systems Expert 02:32 The Evolution of Document Management Systems 05:43 Challenges and Solutions in DMS Adoption 13:06 The Rise of Cloud-Based DMS 21:07 The Future of DMS and AI Integration 36:55 Closing Thoughts Support the show

Send us Fan Mail 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 research is reshaping the legal field.  00:00 Introduction and Welcome 00:41 Guest Introduction: Dr. Megan Ma 01:31 Personal News and AI Analogies 05:09 Research on Multi-Agent Simulations 09:02 Training and Customization of AI Agents 16:34 Risk Mitigation and Future Directions 22:55 Challenges and Collaborations in AI Research 25:52 Introduction to Generative Agents 26:15 Simulating Human Behavior in AI 27:18 Applying AI in Legal Domain 29:10 Innovative Legal Tools 31:53 Personality and Subjectivity in Law 34:15 Evaluating AI and Human Collaboration 37:03 Future of AI in Legal Practice 43:33 Challenges and Opportunities in AI Training 44:27 AI as Companions and Counselors 49:34 Conclusion and Final Thoughts Support the show