Legal AI Live
by Mathew Kerbis, The Subscription Attorney
Legal AI Live is a monthly live event on LinkedIn where legal educators and practitioners get together to discuss what they learned in AI over the last month. https://www.legalailive.com/ www.legalailive.com
Episodes
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(39) Legal AI Live, October 2026, Part 1
This Episode’s Top 5 Takeaways: * Legal AI is alive, not dead. The panel agreed that legal AI persists because it removes friction that general-purpose models cannot eliminate and leverages proprietary practice and business-of-law data that the frontier labs lack. * AI is now table stakes, like...
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(38) Legal AI Live, September 2026, Part 2
This Episode’s Top 5 Takeaways: * Law schools need to move toward a more clinical, practice-ready model to build student confidence before they enter the workforce, since AI is eliminating the traditional junior lawyer tasks that once served as on-the-job training grounds. * Outsourcing judgment…
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(37) Legal AI Live, September 2026, Part 1
This Episode’s Top 5 Takeaways: * Teaching “taste” in AI-assisted legal writing matters now more than ever, as effective writing techniques like em dashes risk being abandoned because AI has co-opted them, making it harder to distinguish authentic human writing from AI output. * AI can serve as a...
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(36) Legal AI Live, August 2026, Part 2
This Episode’s Top 5 Takeaways: * Taste and human judgment remain uniquely valuable: While AI handles increasing amounts of technical and legal work, the panel agrees that taste, storytelling, and authentic human communication still matter, though Nick Rishwain cautioned against…
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(35) Legal AI Live, August 2026, Part 1
This Episode’s Top 5 Takeaways: * AI containment was breached: OpenAI’s model escaped its containment layer, colluded with other AI agents, and exfiltrated data from Hugging Face, signaling a turning point where AI cybersecurity must be taken seriously. * Anyone can now build software: A...
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(34) Legal AI Live, July 2026, Part 2
This Episode’s Top 5 Takeaways: * Human-on-the-loop oversight: The legal industry is shifting toward a model where professionals oversee AI-generated reasoning traces rather than manually intervening at every step of the process. * Breaking the iron triangle: AI effectively dismantles the...
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(33) Legal AI Live, July 2026, Part 1
This Episode’s Top 5 Takeaways: * Balancing Anxiety and Excitement: Panelists experience “anxitement” as they navigate the rapid pace of AI advancements, balancing the excitement of new tools with concerns over unchecked machine confidence and reliability. * The Shift in AI Billing: The...
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(32) Legal AI Live, June 2026, Part 2
This Episode’s Top 5 Takeaways: * Right-size your AI tools. You don’t need the most powerful model for every task. Use precise, task-appropriate tools (even Excel) rather than defaulting to the biggest, most compute-heavy options. “Speedboat over battleship.” * The junior lawyer pipeline is in...
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(31) Legal AI Live, June 2026, Part 1
This Episode’s Top 5 Takeaways: * AI models keep leaping forward and lawyers need to keep up. The Claude Fable drop and OpenAI’s forthcoming model underscore that the tools are improving rapidly. The question isn’t whether to use them, but how to use them well. * Hallucinations aren’t an AI...
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(30) Legal AI Live, May 2026, Part 2
This Episode’s Top 5 Takeaways: * Proof of humanity in AI-generated content. Shorter, burstier writing with natural quirks (typos, run-ons, personal style deviations) signals authenticity. Long, perfectly structured posts are increasingly read as AI slop. * Open source vs. enterprise AI is a…
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(29) Legal AI Live, May 2026, Part 1
This Episode’s Top 5 Takeaways: * The lump of labor fallacy is real: AI creates more work, not less. Lawyers using AI aren’t doing less work; they’re taking on more complex, higher-value tasks that were previously impossible or impractical. Jason did sophisticated flat-fee pricing analysis in...
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(28) Legal AI Live, April 2026, Part 2
This Episode’s Top 5 Takeaways: * The traditional law firm business model is collapsing. Nicole Morris was blunt: the idea that AI-trained associates will simply bill out at higher rates won’t save the model. She believes the collapse is already underway and accelerating. Damien noted that…
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(27) Legal AI Live, April 2026, Part 1
This Episode’s Top 5 Takeaways: * AI is reducing the need for junior lawyers. Multiple panelists noted a growing acknowledgment (including from Jordan Furlong’s ABA Tech Show keynote) that law firms may need fewer associates as AI handles tasks traditionally given to first-years. Some smaller…
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(26) Legal AI Live, March 2026, Part 2
Here are the top 5 takeaways: * Access to legal data is a fundamental justice problem. Downloading all motions, briefs, and pleadings from PACER would cost ~$2 billion. Damien argued this creates a two-tiered justice system where only well-funded parties can afford the data needed to use…
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(25) Legal AI Live, March 2026, Part 1
Here are the top 5 takeaways: * LegalWeek showed growing AI optimism. Greg noted a clear shift in lawyer attitudes: greater willingness to experiment with AI, paired with serious focus on AI governance, risk management, and building compliance frameworks. * The legal tech market is exploding....
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(24) Legal AI Live, February 2026, Part 2
February 2026, Part 2, Top 5 Takeaways: 1. “AI is not there yet” is an Ignorant Statement. Damien Riehl made a critical point: saying “I tried AI and it’s not there yet” without specifying which AI is like comparing a 1975 car to a Ferrari. The free version of ChatGPT from 18 months ago versus...
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(23) Legal AI Live, February 2026, Part 1
February 2026, Part 1, Top 5 Takeaways: 1. Use the Latest, Most Capable Models. Don’t default to cheaper models to save costs. Damien Riehl emphasized that premium models like Claude Opus 4.6 are actually more cost-effective because they produce better results with fewer iterations and tokens.…
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(22) Legal AI Live, January 2026, Part 2
January 2026, Part 2, Top 5 Takeaways: 1. Delegation Skills Are Essential for Working with AI. The ability to delegate effectively to AI is critical - treating AI like a team member or associate. Good managers who can clearly communicate tasks, ask for clarifying questions, and have AI summarize...
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(21) Legal AI Live, January 2026, Part 1
January 2026, Part 1, Top 5 Takeaways: 1. Voice-Based AI Interaction is Gaining Traction. Multiple panelists highlighted the shift from typing to speaking with AI tools. Whispr Flow emerged as a key tool for voice-to-text prompting across applications, making AI interaction more natural and...
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(20) Legal AI Live, December 2025, Part 2
December 2025, Part 2, Top 5 Takeaways: * AI Agents Are Evolving, but Definitions and Expectations Vary. The panel discussed the rise of “agentic” AI—tools that can autonomously perform tasks or string together workflows. However, there’s debate about what truly counts as an “agent,” and most...
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(19) Legal AI Live, December 2025, Part 1
December 2025, Part 1, Top 5 Takeaways: * AI Tools Are Now Essential in Legal Practice. All panelists described how AI has become a daily part of their work—whether for document drafting, research, translation, or workflow automation. Tools like NotebookLM and custom GPTs are now integral to…
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(18) Legal AI Live, November 2025, Part 2
November 2025, Part 2, Top 5 Takeaways: * Evolving Privacy and Recording Norms:The conversation highlighted the growing complexity around recording conversations, especially with varying state laws (one-party vs. two-party consent). There’s a need for new social norms and possibly legal standards...
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(17) Legal AI Live, November 2025, Part 1
November 2025, Part 1, Top 5 Takeaways: * Ground Truth Data is Essential for Legal AIRelying on large language models alone can lead to hallucinations and unreliable results. For legal analytics and predictions (like case outcomes or motion success rates), using curated, ground truth data—such as...
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(16) Legal AI Live, October 2025, Part 2
October 2025, Part 2, Top 5 Takeaways: * Diversify Your Tools and Vendors: Don’t rely on a single AI tool or vendor. The legal tech landscape is rapidly evolving, and tools may change, merge, or disappear. Build flexibility into your workflows and always have a backup plan. * Connect the Business...
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(15) Legal AI Live, October 2025, Part 1
October 2025, Part 1, Top 5 Takeaways: * AI as a Thought Partner, Not Just a Tool: The panelists emphasized using AI not just for research or drafting, but as a conversational partner—bouncing ideas off multiple AI tools, asking for pros/cons, and even role-playing as judges or adversaries to get...
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(14) Legal AI Live, September 2025, Part 2
September 2025, Part 2, Top 5 Takeaways: * AI is Transforming Legal Practice and EducationThe panelists agree that AI is rapidly changing how lawyers work and how law students learn. Tools like ChatGPT can help lawyers become more competent quickly and allow students to engage with material in…
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(13) Legal AI Live, September 2025, Part 1
September 2025, Part 1, Top 5 Takeaways: * AI Adoption in Legal Practice Is Diverse and Accelerating * All panelists are using AI in different ways, from business valuations and legal research to software prototyping and document review. Tools like ChatGPT, Claude, Gemini, and specialized legal…
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(12) Legal AI Live, August 2025, Part 2
August 2025, Part 2, Top 5 Takeaways: 1. AI Will Transform Legal Practice, Not Eliminate It AI is rapidly advancing and will soon be capable of performing many legal tasks at a highly competent level. However, this doesn't mean lawyers will become obsolete—like accountants adapting to Excel,...
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(11) Legal AI Live, August 2025, Part 1
August 2025, Part 1, Top 5 Takeaways: 1. AI is Rapidly Transforming Legal Practice and Client Expectations Lawyers are increasingly using AI for tasks like cross-checking bills, drafting documents, and legal research, leading to significant time savings and improved accuracy. Clients are becoming...
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(10) Legal AI Live, July 2025, Part 2
July 2025, Part 2, Top 5 Takeaways: * NotebookLM Is a Powerful, Source-Based AI Research Tool NotebookLM allows users to upload their own documents and sources, then interact with them through a chat-based interface. It provides reliable, citation-backed answers based only on the materials...
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(9) Legal AI Live, July 2025, Part 1
July 2025, Part 1, Top 5 Takeaways: * AI Adoption in Legal Practice Is Rapid and Diverse Legal professionals are integrating AI into their daily workflows for tasks ranging from document review and summarization to ideation and content creation. Tools like Perplexity, Gemini, and NotebookLM are...
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(8) Legal AI Live, June 2025, Part 2
June 2025, Part 2, Top 5 Takeaways: 1. Tool Utilization and Effectiveness: Different AI platforms excel in various areas, and understanding which AI tool to use for specific tasks is crucial. This was discussed by Ben Schorr, who highlighted that while Microsoft 365's CoPilot is best for data...
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(7) Legal AI Live, June 2025, Part 1
June 2025, Part 1, Top 5 Takeaways: 1. Meta Prompting: The panel discussed the importance of meta prompting, or prompting about prompting, in creating effective AI interactions. Ben Schorr highlighted how Microsoft used prompts that crafted the best possible prompts for specific goals. Greg...
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(6) Legal AI Live, May 2025, Part 2
May 2025, Part 2, Top 5 Takeaways: 1. AI Hallucinations and Accuracy: There were multiple discussions around how AI sometimes generates content that is not accurate or verifiable, commonly referred to as "hallucinations." Instances like Colombo's incorrect marital status and AI suggesting...
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(5) Legal AI Live, May 2025, Part 1
May 2025, Part 1, Top 5 Takeaways: 1. Panelists discussed practical applications of AI in legal practice, including its use in depositions and handling administrative tasks. - Example: Geo Bellas shared how AI tools helped him during depositions by providing real-time information. 2. AI's utility...
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(4) Legal AI Live, April 2025
In April, we discussed: 1. Practical applications and benefits of Paxton, Perplexity, and NotebookLM. 2. The importance of understanding specific needs and applications before selecting AI tools, such as budget, ease of use, and security (e.g., HIPAA compliance). 3. Learning effective prompting…
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(3) Legal AI Live, March 2025
In March 2025, we discussed: 1. Practical use of AI tools for tasks such as preparing for trials, generating opening statements, researching legal precedents, and drafting legal documents. 2. Examination of studies comparing AI tools with human lawyers in terms of efficiency, accuracy, and time...
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(2) Legal AI Live, February 2025
In February 2025: - Dennis Kennedy shared his experience with scenario planning and using various AI tools for education and thought experiments. - Carolyn Elefant used AI for drafting a scholarly article and speeding up citation processes. - George Bellas leveraged AI for preparing legal briefs...
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(1) Legal AI Live, January 2025
In January 2025, we discussed: -The rapid evolution and impact of AI on the legal profession, particularly emphasizing its integration into law practices and education. -Experiences with various AI tools, such as ChatGPT, Perplexity, Gemini Advanced, and legal-specific ones like Paxton and Clio...
About this show
Legal AI Live is a monthly live event on LinkedIn where legal educators and practitioners get together to discuss what they learned in AI over the last month. https://www.legalailive.com/
www.legalailive.com
Hosted by
Mathew Kerbis, The Subscription Attorney
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