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 the broader societal implications of AI-driven legal services.

00:00 Big Tech and Big Law
00:46 AI's Impact on Legal Industry
01:21 The AI Tsunami
02:52 Future of Legal Bots
03:18 Challenges of Data Collection
03:57 Human Element in AI
07:29 AI Reasoning and Interpretability
13:53 Big Players in Legal Tech
19:32 Specialized Legal Models
22:08 Adobe's Move into Legal Tech
23:46 The Unauthorized Practice of Law and Big Tech
24:49 Legal Tech Companies and the UPL Debate
27:06 Legal Information vs. Legal Advice
28:57 The Future of Legal Services and AI
35:27 Strategies for Law Firms, Incumbents, and Startups

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 proprietary data, and the potential revolution in providing legal services. Whether you’re from a law firm, in-house counsel, or a legal tech vendor, this episode offers key insights into navigating the future of the legal industry.

00:00 Introduction and Welcome
00:10 Reflections on Legal Week
00:31 Marketing Highlights and Critiques
01:17 The Role of Large Language Models
01:53 VC Expectations and Industry Challenges
03:01 Differentiation in Legal Tech
04:24 Importance of Proprietary Data
06:39 Capturing Expert Knowledge
08:13 The Future of Legal Workflows
17:48 In-House Counsel and Knowledge Management
20:43 The Buzz Around Agents and Workflows
23:49 Pivoting to Jane on Day 30
24:27 The Role of AI in Legal Tech
25:42 Public vs. Private Data in Legal Tech
26:46 The Value of Legal Tech Products
28:13 Buyer Behavior in the Legal Tech Market
31:04 The Competitive Landscape of Legal Services
32:57 Core, Cream, and Commodity Legal Work
35:31 Future Actions for Legal Tech Players
38:14 Optimism and Pessimism in AI Development
42:35 Legal Information vs. Legal Advice
44:41 Conclusion

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 adopting AI, and the evolving marketplace. They also touch on the influence of AI on billing models, access to justice, and the importance of transparency.

If you're fascinated by the evolution of generative AI usage in law firms, you won't want to miss this episode.

00:00 Introduction: Helder Santos from Bird and Bird

00:53 Choosing Legora: The Decision-Making Process

02:54 Build vs. Buy: Strategic Considerations

05:54 Integrating AI: Challenges and Successes

08:21 Evaluating AI Vendors: Criteria and Transparency

11:42 Adoption and Training: Lawyer's Perspectives

17:23 Future of AI in Law: Optimism and Challenges

23:24 Closing Thoughts

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 intelligence, the importance of data, and the intersecting roles within law firms. Tune in to hear valuable insights on demonstrating value to skeptical lawyers and the future of legal tech.

00:00 Introduction

00:46 The Role of Rainmakers in Law Firms

01:56 The Power of Storytelling in Sales

02:48 Challenges in Legal Tech and CRM Solutions

05:17 Understanding Law Firm Dynamics

08:16 Effective Sales Strategies and Personas

09:28 The Importance of Data in CRM

14:50 Roles and Profitability in Law Firms

17:34 Understanding the Dynamics of Messaging

18:10 Challenges of Selling to Law Firms

18:53 Crafting a Compelling Story

19:41 Startup Storytelling Strategies

20:23 Product Market Fit and Storytelling

20:38 Understanding Market Personas

21:47 Tailoring Messages for Different Legal Personas

23:12 The Importance of Data in Legal Tech

23:52 Solving Small Problems to Expand Market

29:43 Demonstrating Value to Skeptical Lawyers

30:24 Optimism in Legal Tech

34:31 Closing Thoughts and Reflections

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).

Catherine, Damien, and Horace explore how LLMs can augment document automation, the ethics of legal tech processes, and the evolving landscape of legal tech solutions.

Catherine's clarity and depth make this episode a must-watch for anyone interested in the intersection of law and technology.

DeepSeek has been all the rage among the tech community in January 2025. In this episode, Damien and Horace are joined by special guest Joe Rayment, CEO of Automatise, to explore the implications of DeepSeek.

The discussion covers a range of topics including the geopolitical aspects, build vs buy considerations, licensing and terms of use, cost reduction, data privacy, vendor lock-in, and the skills gap for law firms and legal tech vendors. The conversation delves into the potential impacts, benefits, and challenges that DeepSeek poses for the legal tech industry.

Join Horace and Damien as they return from a break to a deep dive discussion with Adrian Parlow, founder and CEO of Point One, on the significance and future of timekeeping in law firms. They explore the persistence of the billable hour, the potential shift towards flat fees, and the role of AI in automating time entries. The conversation delves into how accurate time data can transform law firm efficiency, pricing, and the overall practice, with a spotlight on standardization through systems like SALI.

00:00 Welcome Back!

02:00 The Future of the Billable Hour

04:18 The Importance of Time Data

07:54 Challenges in Timekeeping

13:07 AI and Automation in Law Firms

15:29 Transitioning to Flat Fee Models

24:21 Standardizing Legal Data

30:39 Looking Ahead: The Future of Time Keeping

35:15 Closing Remarks

In this episode of Further Comments, we welcome legal tech expert Stephanie Wilkins to discuss the highlights and transformative trends in legal technology from 2024. We reflect on the TLTF conference in Miami, explore the adoption of AI in the legal industry, and contemplate the evolving market dynamics, including the rise of the mid-market law firms. The discussion also covers the future predictions for 2025, user experiences, and the impact of generative AI on legal practices.

Tune in for another dive into the world of legal tech!

00:00 Introduction

00:29 Recap of the TLTF Summit

01:13 Introducing Stephanie Wilkins

01:49 Highlights of 2024

04:20 Discussion on Legal Tech Adoption

15:17 Mid Market Law Firms and Technology

23:23 Predictions for 2025

29:26 Final Thoughts