

Further Comments
Damien Riehl & Horace Wu
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
Mentioned books

Mar 31, 2025 • 45min
Everything We Didn't Learn at Legalweek 2025
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 Welcome00:10 Reflections on Legal Week00:31 Marketing Highlights and Critiques01:17 The Role of Large Language Models01:53 VC Expectations and Industry Challenges03:01 Differentiation in Legal Tech04:24 Importance of Proprietary Data06:39 Capturing Expert Knowledge08:13 The Future of Legal Workflows17:48 In-House Counsel and Knowledge Management20:43 The Buzz Around Agents and Workflows23:49 Pivoting to Jane on Day 3024:27 The Role of AI in Legal Tech25:42 Public vs. Private Data in Legal Tech26:46 The Value of Legal Tech Products28:13 Buyer Behavior in the Legal Tech Market31:04 The Competitive Landscape of Legal Services32:57 Core, Cream, and Commodity Legal Work35:31 Future Actions for Legal Tech Players38:14 Optimism and Pessimism in AI Development42:35 Legal Information vs. Legal Advice44:41 Conclusion

Mar 17, 2025 • 28min
How I Met Legora (ft Helder Santos)
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 Bird00:53 Choosing Legora: The Decision-Making Process02:54 Build vs. Buy: Strategic Considerations05:54 Integrating AI: Challenges and Successes08:21 Evaluating AI Vendors: Criteria and Transparency11:42 Adoption and Training: Lawyer's Perspectives17:23 Future of AI in Law: Optimism and Challenges23:24 Closing Thoughts

Feb 28, 2025 • 35min
The one about selling stories (ft Ben Chiriboga)
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 Introduction00:46 The Role of Rainmakers in Law Firms01:56 The Power of Storytelling in Sales02:48 Challenges in Legal Tech and CRM Solutions05:17 Understanding Law Firm Dynamics08:16 Effective Sales Strategies and Personas09:28 The Importance of Data in CRM14:50 Roles and Profitability in Law Firms17:34 Understanding the Dynamics of Messaging18:10 Challenges of Selling to Law Firms18:53 Crafting a Compelling Story19:41 Startup Storytelling Strategies20:23 Product Market Fit and Storytelling20:38 Understanding Market Personas21:47 Tailoring Messages for Different Legal Personas23:12 The Importance of Data in Legal Tech23:52 Solving Small Problems to Expand Market29:43 Demonstrating Value to Skeptical Lawyers30:24 Optimism in Legal Tech34:31 Closing Thoughts and Reflections

Feb 14, 2025 • 50min
A Love Letter to Document Automation and Process Improvement (ft Catherine Bamford)
Catherine Bamford, a legal tech expert known as the 'Duchess of Document Automation', shares her insights on revolutionizing legal processes through technology. She dives into the challenges law firms face with document automation and the importance of tailored solutions. The discussion highlights the integration of large language models in legal drafting, emphasizing the essential role of human expertise. Catherine also addresses billing disparities in legal services and the potential of playbooks to streamline practices, making for a fascinating exploration of the future of law and technology.

Feb 3, 2025 • 42min
DeepSeek and the Seven Dwarf Problems for LegalTech (ft Joe Rayment)
Join Joe Rayment, CEO of Automatise, an Australian legal tech expert, as he dives into the buzz around DeepSeek, a revolutionary AI language model. He tackles the dynamic between open-source and proprietary tech, emphasizing the impact on the legal landscape. Rayment discusses the financial and ethical implications of DeepSeek, exploring data ownership and vendor lock-in challenges. He also highlights the geopolitical narratives behind AI advancements and raises awareness of the nuanced risks in machine learning and cybersecurity for legal firms.

Jan 14, 2025 • 36min
Should Auld Time Billing Be Forgot (ft Adrian Parlow)
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 Hour04:18 The Importance of Time Data07:54 Challenges in Timekeeping13:07 AI and Automation in Law Firms15:29 Transitioning to Flat Fee Models24:21 Standardizing Legal Data30:39 Looking Ahead: The Future of Time Keeping35:15 Closing Remarks

Dec 16, 2024 • 33min
These Little Piggies Went To The LegalTech Market (ft Stephanie Wilkins)
In this engaging conversation, legal tech expert Stephanie Wilkins shares her insights on the transformative trends shaping the industry in 2024. She dives into the highlights from the TLTF conference, the rising influence of AI, and the dynamic shifts in mid-sized law firms. Wilkins also discusses predictions for 2025, focusing on how generative AI may redefine billing practices. The episode is packed with valuable perspectives on the future of legal technology and its impact on legal services.

Dec 3, 2024 • 33min
A Tag Astray Keeps Adopters Away
In this episode of 'Further Comments', hosts Horace Wu and Damien Riehl engage in a lively discussion on the eve of Thanksgiving (which coincides with Horace's birthday) about increased adoption of generative AI in legal practices, tagging systems in data management, and the complexities of implementing such systems effectively. They also explore the implications of legal technologies as integral components of society's operating system.

Nov 18, 2024 • 51min
Fear and Leveraging Las Agents (ft Jason Barnwell)
In this discussion, Jason Barnwell, a lawyer and engineer specializing in law and technology, unpacks the intersection of AI and legal practices. He clarifies the often misunderstood landscape of AI agents, moving from engineering constructs to philosophical concepts. There's emphasis on the need for transparency and human oversight in legal tech. Barnwell also highlights how tools like ChatGPT can revolutionize tasks, while balancing human cognition with machine intelligence for optimized data use in product design.

Nov 5, 2024 • 42min
You Gotta Fight For Your Right To Standardize Language (ft Electra Japonas)
Electra Japonas, a legal tech innovator and founder of 1NDA, dives into the vital role of standardizing legal documents to boost efficiency in the law sector. She explores the challenges and historical context of creating uniform contracts, especially NDAs. Japonas advocates for a collaborative approach, influenced by generative AI. The discussion also touches on the balancing act between artistic legal documentation and the push for standardized practices, alongside how the transition to tech-enhanced models is reshaping the legal landscape.


