Fringe Legal Presents Bots @ Work

Hosted by Abhijat Saraswat

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May 2026

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Bots at Work is the new season from Fringe Legal, which explores how AI is changing the way work gets done, with a focus on real-world impact over hype. It looks at how operators, builders, and leaders are using AI to reshape workflows, decision-making, and business models, especially in professional services like law. The show focuses on practical insights, emerging patterns, and honest conversations about what works, what doesn’t, and what comes next as intelligence becomes cheaper and more embedded in everyday work.

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May 15, 2026Episode 446 min

How I built a law firm with AI agents with Helen Fan

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 realiseThe 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 systemsThe Legal AI Value Stack — five levels of AI maturity in law, and why most firms are still stuck at the bottom twoHow Big Law and AI-native firms are competing on entirely different timelines, and why the boutique model might be the one that actually movesWhat Helen is telling firms just starting out: start with mindset, build the orchestration layer, and don't skip workflow integrationTimestamps:00:00 — Helen's OpenClaw Law LLP experiment: what an AI-native law firm looks like in practice02:20 — Agent-to-agent communication and argument reports: why they reduce hallucinations04:10 — Stability, troubleshooting, and the real cost of open-source frameworks07:00 — The Legal AI Value Stack: five levels of AI maturity and where the moats actually are12:00 — Why most firms are still at level one or two16:00 — Proprietary data and the scaling wall19:00 — Big Law vs AI-native firms: speed, trust, and structural barriers23:00 — Guardrails, verification, and building an orchestration layer that holds34:00 — Vendor moats, platform plays, and what M&A in legal AI actually looks like39:00 — What makes a law firm genuinely AI-native, not just AI-curious43:00 — Where to start: mindset, workflow, and infrastructure44:50 — Final thoughts on the pace of change and what to watch nextResources:Helen Fan on LinkedIn — follow her 100 Days of AI Law experiment as it unfoldsThe Legal AI Value Stack — Helen's five-stage framework, published on her Substack, Helen's Legal AI LabOpenClaw Framework — the open-source multi-agent system Helen built OpenClaw Law LLP onClaude AI — the AI tool Helen uses for legal and strategic workAI-Native Law Firm Index — a running list of AI-native law firms referenced in the episode

May 7, 2026Episode 341 min

How a Lawyer Beat 13,000 People to Win Anthropic's Biggest Hackathon

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 experienceHow curiosity, strategic prompts, and optimizing workflows accelerate AI adoptionThe importance of context engineering and planning in AI projectsPractical tips for legal professionals to learn AI fast, including a one-week crash courseWhy model upgrades like Opus 4.7 can dramatically boost productivity overnightManaging sensitive data and confidentiality when working with AI-driven legal workflowsThe future of law firms and legal teams in a world increasingly driven by AI and automationQuick tips on integrating voice tools like Wisprflow into daily legal practiceTimestamps:00:00 - The defining moment: How a lawyer beat 13,000 applicants at a hackathon02:48 - What is Cursor? A straightforward guide for non-developers entering AI-driven workflows04:14 - Creative backgrounds fueling AI exploration — from Hollywood to law05:43 - Overcoming the learning curve in AI — a disciplined one-week challenge07:19 - Building skills with prompt engineering — turning prompts into productivity tools09:14 - The exponential improvements in AI models — what today’s upgrade means11:11 - Handling complex projects: from blueprints to AI vision processing13:39 - The California permit system problem — using AI to cut permit delays15:57 - Managing token limits and context: technical tips from a seasoned AI builder19:22 - The impact of new model drops on projects — building for the future, not today20:36 - Voice productivity tools — Whisper Flow and voice mode in AI workflows22:38 - Planning your AI projects like a lawyer — IRAC prompts and adversarial prompting25:15 - How AI might reshape legal team structures and company management33:03 - Maintaining human agency in AI-powered days: asset or risk?34:21 - Favorite AI tools — Wisprflow and Claude Code35:08 - Tasks ripe for automation — focus on what makes you uniquely human37:28 - Common AI mistakes: The trap of "locking in" on current models38:46 - Building a future-proof legal skillset: prompt mastery and context management39:52 - Starting today: passions + low-stakes AI experiments as growth strategies40:58 - Connect with Michael T. Brown: LinkedIn & ongoing projects

April 30, 2026Episode 244 min

The Secret to Building Resilient Legal Tech Teams with Jennifer Waite

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 OfficerThe evolution of the Knowledge Management department at a law firmEffective vendor collaboration and partnership strategiesHow AI is transforming legal workflows and team cultureBalancing innovation with governance and securityManaging AI tools, costs, and ethical considerationsBuilding skills for future relevance in legal careersPractical 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 firmResources & Links:Perplexity AIClaude AI by Anthropic Truth SystemsLupl Connect with Jennifer Waite:LinkedIn

April 16, 2026Episode 143 min

AI Alone Isn't Enough for Law Firms with Ted Theodoropoulos

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"Vibe-coded apps aren't replacing anything that's rolled out in the enterprise. Even just maintaining compliance with SOC 2, there are certain SDLC processes which have to be followed." — Ted"Many leaders in the business of law functions were literally hand-picked because of their resistance to change. Now we're telling them: change everything with GenAI and move to the cloud. Is that the best person to be sitting in that seat?" — Ted"Law firms spend 2.4% of revenue on all technology. Professional services peers spend about twice that." — Ted"If you fail at change management, it doesn't matter how good your tech is. The project will not succeed." — Ted"Empathy specifically is going to be a core skill set as the technology delivers more and more of the legal work product." — TedTimestamps00:00 Vibe coding: what it is, where it works, where it breaks09:12 Enterprise disruption and the collaboration model that actually works15:20 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 differently27:34 From bespoke services to SaaS: InfoDash's transformation story33:24 Forward-deployed engineers, high-touch delivery, and the future of collaboration tools40:07 Measuring AI success and the soft skills lawyers need to build

May 5, 2025Episode 228 min

Responsible AI in Law: Building Frameworks, Use Cases, and Trust with RAILS

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.TakeawaysRAILS 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.Chapters00:00 Introduction to Rails and Responsible AI01:57 Understanding Rails: Origins and Objectives05:55 Working Groups: Focus Areas and Contributions09:54 The Importance of Responsible AI in Legal Services13:46 Outputs and Resources from Rails17:56 Use Cases: Development and Significance22:04 Future Directions for Rails and AI Literacy

January 16, 2025Episode 137 min

Practice, Profit, Power: James Markham and Darren Mee of The Legal MBA

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

September 3, 2024Episode 321 min

Balancing Technology and Human Connection in Legal Services with Joey Seeber

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

February 14, 2024Episode 233 min

Law Firm Revenue Management with Ayora.ai - The $36 Billion Opportunity

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 notes00:02 Introduction to the Fringe Legal Podcast00:29 Guest Introduction: Stefan Ciesla, Co-founder and CEO of Ayora00:58 Steven's Background and Ayora's Founding Team02:07 The Unique Blend of Ayora's Founding Team02:55 Understanding Ayora's Mission and Purpose04:24 The Role of Lawyers as Revenue Managers04:43 The Impact of Decision-Making on Revenue Management08:28 Introducing Ayora's Smart Lockup Assistant20:20 The Role of AI and Machine Learning in Decision-Making27:05 The Impact of Fixed Fee Work on Revenue Management30:12 Conclusion and Contact Information

January 16, 2024Episode 134 min

Building a tech-enabled culture in law firms

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.

October 12, 2023Episode 743 min

Reinventing Associate Training with Abdi Shayesteh (AltaClaro)

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