Fringe Legal Presents Bots @ Work

Helen Fan has been building an AI-native law firm from scratch, in public, for 50 days. Not a demo. Not a prototype. A real practice with AI agents handling legal strategy and research, and she's documenting every stumble along the way.

In this episode, we get into what that actually looks like: the agents, the arguments, the security concerns, and the hard questions about whether AI-native firms and traditional law firms are on a collision course or just running separate races.

In this episode:

• How Helen built OpenClaw Law LLP with two AI agents, Morgan and Cleo, and why agent-to-agent argument reports matter more than most people realise
• The practical pain of open-source agent frameworks: stability issues, setup overhead, and the security surface that opens up the moment you connect an agent to real systems
• The Legal AI Value Stack — five levels of AI maturity in law, and why most firms are still stuck at the bottom two
• How Big Law and AI-native firms are competing on entirely different timelines, and why the boutique model might be the one that actually moves
• What Helen is telling firms just starting out: start with mindset, build the orchestration layer, and don't skip workflow integration

Timestamps:

00:00 — Helen's OpenClaw Law LLP experiment: what an AI-native law firm looks like in practice
02:20 — Agent-to-agent communication and argument reports: why they reduce hallucinations
04:10 — Stability, troubleshooting, and the real cost of open-source frameworks
07:00 — The Legal AI Value Stack: five levels of AI maturity and where the moats actually are
12:00 — Why most firms are still at level one or two
16:00 — Proprietary data and the scaling wall
19:00 — Big Law vs AI-native firms: speed, trust, and structural barriers
23:00 — Guardrails, verification, and building an orchestration layer that holds
34:00 — Vendor moats, platform plays, and what M&A in legal AI actually looks like
39:00 — What makes a law firm genuinely AI-native, not just AI-curious
43:00 — Where to start: mindset, workflow, and infrastructure
44:50 — Final thoughts on the pace of change and what to watch next

Resources:

• Helen Fan on LinkedIn — follow her 100 Days of AI Law experiment as it unfolds
• The Legal AI Value Stack — Helen's five-stage framework, published on her Substack, Helen's Legal AI Lab
• OpenClaw Framework — the open-source multi-agent system Helen built OpenClaw Law LLP on
• Claude AI — the AI tool Helen uses for legal and strategic work
• AI-Native Law Firm Index — a running list of AI-native law firms referenced in the episode

Most professionals are overlooking a secret weapon that’s transforming workflows and legal practices faster than anyone expected. Mike Brown reveals how a solo lawyer turned AI hobbyist beat out 500 engineers at a high-stakes hackathon—and how this level of creative problem-solving can unlock your team’s potential today.

Starting from scratch, Mike’s curiosity and strategic experimentation with open-source AI tools reshaped his legal practice and built a new frontier in legal tech. He shares concrete tactics—like dedicating just one week to mastering prompting or building modular plans that make complex projects manageable—that anyone can apply now. You’ll discover how to leverage AI as an extension of your reasoning, rather than just a search engine, and how to avoid common pitfalls like token constraints and over-reliance on static models.

In this episode:

• The story behind a lawyer winning a top AI hackathon with minimal coding experience
• How curiosity, strategic prompts, and optimizing workflows accelerate AI adoption
• The importance of context engineering and planning in AI projects
• Practical tips for legal professionals to learn AI fast, including a one-week crash course
• Why model upgrades like Opus 4.7 can dramatically boost productivity overnight
• Managing sensitive data and confidentiality when working with AI-driven legal workflows
• The future of law firms and legal teams in a world increasingly driven by AI and automation
• Quick tips on integrating voice tools like Wisprflow into daily legal practice

Timestamps:
00:00 - The defining moment: How a lawyer beat 13,000 applicants at a hackathon
02:48 - What is Cursor? A straightforward guide for non-developers entering AI-driven workflows
04:14 - Creative backgrounds fueling AI exploration — from Hollywood to law
05:43 - Overcoming the learning curve in AI — a disciplined one-week challenge
07:19 - Building skills with prompt engineering — turning prompts into productivity tools
09:14 - The exponential improvements in AI models — what today’s upgrade means
11:11 - Handling complex projects: from blueprints to AI vision processing
13:39 - The California permit system problem — using AI to cut permit delays
15:57 - Managing token limits and context: technical tips from a seasoned AI builder
19:22 - The impact of new model drops on projects — building for the future, not today
20:36 - Voice productivity tools — Whisper Flow and voice mode in AI workflows
22:38 - Planning your AI projects like a lawyer — IRAC prompts and adversarial prompting
25:15 - How AI might reshape legal team structures and company management
33:03 - Maintaining human agency in AI-powered days: asset or risk?
34:21 - Favorite AI tools — Wisprflow and Claude Code
35:08 - Tasks ripe for automation — focus on what makes you uniquely human
37:28 - Common AI mistakes: The trap of "locking in" on current models
38:46 - Building a future-proof legal skillset: prompt mastery and context management
39:52 - Starting today: passions + low-stakes AI experiments as growth strategies
40:58 - Connect with Michael T. Brown: LinkedIn & ongoing projects

Most legal leaders underestimate how quickly AI will redefine their teams—and why embracing curiosity now is the only way to stay relevant.

In this episode, Jennifer Waite, Chief Knowledge & Innovation Officer at Arnall Golden Gregory, shares her unique journey from librarian to Chief Knowledge and Innovation Officer. She dives into how her early experiences in law and librarianship shaped her approach to knowledge management, technology, and AI in a law firm setting. Whether you're navigating data strategies, vendor relations, or AI adoption, her perspectives offer clarity on building a future-ready legal organization.

In this episode:

• Jennifer's transition from law librarian to Chief Knowledge Officer
• The evolution of the Knowledge Management department at a law firm
• Effective vendor collaboration and partnership strategies
• How AI is transforming legal workflows and team culture
• Balancing innovation with governance and security
• Managing AI tools, costs, and ethical considerations
• Building skills for future relevance in legal careers
• Practical steps for implementing AI from scratch in a law firm's context

Timestamps:
00:00 - Jennifer's unexpected journey from librarian to Chief Knowledge Officer
02:15 - The role of librarians in knowledge management and AI
03:03 - Transition from public service to private legal sector
04:11 - The importance of data strategy and the capstone project impact
05:39 - Evolution of the KM team and departmental shifts over the years
07:08 - Integrating technology, innovation, and governance within legal teams
09:19 - The dynamics of security, governance, and AI innovation working hand-in-hand
11:39 - Building strong vendor relationships and setting expectations
13:55 - Assessing vendor responsiveness and managing costs efficiently
16:12 - Transparency and openness with vendors during AI tool deployment
17:30 - The influence of rapid software updates on vendor decision-making
19:24 - The feasibility of internal development vs. vendor reliance
23:11 - Understanding AI’s true capabilities and common misconceptions
24:24 - Educating users on AI limitations and strengths in legal workflows
28:43 - Managing AI credits, costs, and internal resource allocation
33:16 - How AI can automate repetitive legal tasks in the near future
36:32 - Engaging senior leaders and promoting AI adoption across levels
38:18 - Cultivating curiosity and ongoing learning in legal teams
42:02 - The peril of ignoring AI advancements and the skills law professionals need
44:36 - Practical advice for launching AI in a new or existing legal firm

Resources & Links:

• Perplexity AI
• Claude AI by Anthropic 
• Truth Systems
• Lupl

Connect with Jennifer Waite:

• LinkedIn

Most AI conversations in legal right now are either breathless hype or reflexive skepticism. This one is neither.

Ted Theodoropoulos has spent close to 20 years in legal tech. He's worked with more than half the AmLaw, runs InfoDash (used by about one in four AmLaw firms), and hosts the Legal Innovation Spotlight podcast. He sees what firms are actually buying, where tools actually break, and which firms are actually moving.

We get into vibe coding (what it's good for, where it falls apart), why law firms still spend only 2.4% of revenue on technology, what separates the firms adapting from the firms stalling, and why empathy might be the most undervalued lawyer skill of the next five years.

If you care about AI adoption inside professional services, or you're trying to figure out what to build, buy, or ignore, this one's for you.

Notable quotes

Timestamps

• 00:00 Vibe coding: what it is, where it works, where it breaks
• 09:12 Enterprise disruption and the collaboration model that actually works
• 15:20 Why law firms spend 2.4% on tech (and why it's not enough)
• 22:59 Which firms are moving fast and what they're doing differently
• 27:34 From bespoke services to SaaS: InfoDash's transformation story
• 33:24 Forward-deployed engineers, high-touch delivery, and the future of collaboration tools
• 40:07 Measuring AI success and the soft skills lawyers need to build

This episode explores the RAILS initiative, which focuses on the responsible use of AI in legal services. The guests discuss the origins of RAILS, its working groups, and the importance of ethical AI practices. They highlight recent outputs, including a risk management framework and various use cases, while emphasizing the need for AI literacy in the legal field. The discussion also touches on the future of RAILS and the ongoing evolution of AI in legal contexts.

Thanks to our guests, Kelli Raker, Eli Makus, and Leigh Zeiser.

Watch the video version here.

Takeaways

• RAILS launched to address the ethical use of AI in legal services.
• The initiative aims to bridge gaps in AI understanding among legal professionals.
• Working groups focus on client engagement, direct-to-consumer resources, and corporate legal teams.
• AI presents both opportunities and risks that need careful management.
• Access to AI should be equitable across different legal sectors.
• The risk management framework provides guidance for corporate legal teams.
• Use cases developed by RAILS help illustrate practical applications of AI.
• AI literacy is essential for legal professionals and their clients.
• The conversation emphasizes collaboration and sharing of resources.
• Future developments will continue to evolve as AI technology advances.

Chapters

00:00 Introduction to Rails and Responsible AI
01:57 Understanding Rails: Origins and Objectives
05:55 Working Groups: Focus Areas and Contributions
09:54 The Importance of Responsible AI in Legal Services
13:46 Outputs and Resources from Rails
17:56 Use Cases: Development and Significance
22:04 Future Directions for Rails and AI Literacy

In this episode of Fringe Legal, we host an engaging discussion with James Markham and Darren Mee, authors of 'The Legal MBA.' 

The conversation delves into their backgrounds, the inspiration behind their book, and its key themes. We discuss the importance of a broad business education for legal professionals, the integration of legal technology, and the practical applications of the knowledge shared in their book.  
00:00 Introduction and Guest Welcome 
00:29 Background of the Authors 
01:05 Journey to Writing the Legal MBA 
05:03 The Concept and Content of the Legal MBA 
14:29 Target Audience for the Legal MBA 
21:52 Technology in Law Firms 
26:42 Challenges and Adoption of Legal Tech 
34:22 The Legal MBA Academy and Conclusion

In this episode of Fringe Legal, recorded live from ILTACON 2024 in Nashville, Tennessee, Ab sits down with JoeySeeber, CEO of Level Legal.

Joey discusses the journey and growth of Level Legal over 15 years, starting during the Great Recession. The conversation delves into various aspects of building a business for longevity, maintaining a startup mindset in a small company, and delivering services in a human-centric way.

Joey shares insights on their framework and principles for doing business, client feedback, handling competition, and the role of technology in enhancing efficiency.

Read the episode takeaways at: https://www.fringelegal.com/balancing-technology-and-human-connection-in-legal-services-with-joey-seeber

In this episode of the Fringe Legal podcast, host Ab interviews Stefan Ciesla, the co-founder and CEO of Ayora ai, a startup that focuses on helping law firms manage their revenues and improve the revenue management skills of fee earners such as attorneys and lawyers.

Steven discusses the problem Ayora is solving in the legal industry and the role of lawyers as revenue managers. He explains that fee earners often have to make revenue management decisions throughout a matter's lifecycle, but they may not have the necessary skills or focus on revenue management. Ayora's smart lockup assistant helps fee earners by scanning a firm's data related to matters and providing recommendations on monitoring scope, estimates, budgets, resourcing, outside counsel guidelines, and billing. The assistant pre-drafts emails and provides relevant information to make the decision-making process easier and more efficient. Steven also addresses the challenge of balancing AI and machine learning with human control and building trust in the recommendations made. He emphasizes that Ayora prioritizes transparency and user consent and never takes any action without the attorney's knowledge.

Key takeaways:

• Fee earners in law firms, such as attorneys and lawyers, often need to make revenue management decisions throughout a matter's lifecycle but may not have the necessary skills or focus on revenue management.
• Ayora's smart lockup assistant helps fee earners monitor scope, estimates, budgets, resourcing, outside counsel guidelines, and billing, providing recommendations and pre-drafting emails to make decision-making easier and more efficient.
• Ayora prioritizes transparency and user consent, ensuring that attorneys have control over the recommendations made by the system.

Uncommon learning
The legal industry may be missing out on billions of dollars of additional value due to suboptimal revenue management decisions.

Podcast show notes

00:02 Introduction to the Fringe Legal Podcast

00:29 Guest Introduction: Stefan Ciesla, Co-founder and CEO of Ayora

00:58 Steven's Background and Ayora's Founding Team

02:07 The Unique Blend of Ayora's Founding Team

02:55 Understanding Ayora's Mission and Purpose

04:24 The Role of Lawyers as Revenue Managers

04:43 The Impact of Decision-Making on Revenue Management

08:28 Introducing Ayora's Smart Lockup Assistant

20:20 The Role of AI and Machine Learning in Decision-Making

27:05 The Impact of Fixed Fee Work on Revenue Management

30:12 Conclusion and Contact Information

In this episode of the Fringe Legal podcast, host Ab chats with Conan Hines, Director of Legal Technology at Fried Frank, about building a tech-enabled culture in law firms. Conan shares insights from his previous roles at Clifford Chance and other law firms, highlighting the importance of understanding the role of legal technology and the psychology and behavior of users when it comes to successful adoption and change management.

Conan emphasizes the need for building trust with lawyers and finding those who are curious and open to tech-enabled solutions. He suggests starting small with bite-sized engagements to build trust over time. He also discusses the value of creating a foundation for tech adoption and balancing short-term impact with long-term goals.

The conversation delves into the role of vendors in adoption, with Conan highlighting the need for a strong partnership and a transparent framework for success. He stresses the importance of vendors having a real adoption strategy and sharing learnings from what has worked in the past.

Ab and Conan also discuss the challenge of incentives and tracking adoption. They explore the idea of integrating technology training into legal training to emphasize the value and importance of tech skills for lawyers. Ultimately, the key to successful adoption and building a tech-enabled culture in law firms lies in trust, continuous communication, and demonstrating the value of technology.

Key takeaways:

• Building a tech-enabled culture requires understanding the role of legal technology and the psychology and behavior of users.
• Trust is essential for successful adoption. Lawyers need to believe that tech solutions can help them.
• Adoption plans should be simplified and tailored to individual users.
• Integration of technology training into legal training can help emphasize the value of tech skills for lawyers.
• Vendors should have a strong adoption strategy and share learnings from past successes.

Uncommon learning:

Tech adoption requires a partnership between law firms and vendors, with a focus on transparency and continuous communication.

While technology races ahead, improving legal training and education has lagged behind. Law schools excel at teaching students the law, but critical and practical skills development is often lacking. With the traditional law firm apprenticeship model fading, junior lawyers frequently lack opportunities to gain hands-on experience.

Abdi Shayesteh, founder and CEO of the legal training platform AltaClaro, is on a mission to close this practical skills gap. Frustrated by the inefficiencies he experienced firsthand as a junior lawyer, Abdi has reinvented legal education and training. AltaClaro leverages experiential learning techniques rooted in education science to provide associates with hands-on practice on simulated legal matters.

Show Notes

• [00:01:14] Abdi's early entrepreneurial experiences managing a cafe and starting a t-shirt business in college
• [00:08:02] Why Abdi decided to start another company after previous exits
• [00:10:25] Overview of what AltaClaro does
• [00:17:38] Issues with the traditional law firm training model
• [00:23:00] Explanation of the learning science principles AltaClaro leverages
• [00:34:59] Training trends Abdi sees law firms requesting for 2023