Further Comments

Send us Fan Mail

Damien Riehl and Horace Wu catch up in a rapid-fire discussion of recent legal tech and AI news, starting with Damien’s experience using a Tesla Model Y with full self-driving and then moving into whether lawyers should return to X with a curated legal tech feed. 

They discuss OpenAI’s move into legal, Relativity’s stated preference for partnering with major AI labs over newer vendors like Harvey and Legora, and the crowded field of legal AI companies. They explore MCP workflow integration, neuro-symbolic AI, and the resurgence of ontologies and knowledge graphs, including SALI and FOLIO and the high cost of ontology engagements. They cover rising KM/AI roles in law firms, the shift of Harvey and Legora toward in-house tools like “Intake,” Damien’s AI-built litigation visualization web app for an easement dispute, and the Thomson Reuters v. ROSS decision on AI training and fair use, ending with optimism about productivity gains and a renewed focus on liberal arts as AI advances.

00:00 Life Update and Tesla
01:25 Legal Tech on X
03:15 Labs Enter Legal
06:10 MCP and Standards
09:37 Ontologies Come Back
12:00 KM Talent Boom
15:44 Vibe Coding Magic
19:20 Data and Skills Moat
22:02 AI Consciousness Debate
23:54 Bot Calls and Turing Tests
24:51 Persona Driven Argumentation
26:04 Narrowcasting Product Taste
28:53 Harvey and Legora Shift In House
33:03 Building a Litigation Web App
36:39 Data as Legal Advantage
38:45 Thomson Reuters v ROSS Fallout
43:11 Copyright and Tacit Knowledge
44:09 Optimism for AI and Liberal Arts

Support the show

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