Legal AI Live

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

  1. 5d ago

    (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 powerful oversight tool for in-house legal teams, as demonstrated by Jasmine’s custom Glean skill that scans Slack daily for data privacy and compliance risks, giving her a color-coded triage report to manage legal review at the pace of AI development. * Editorial workflows are being streamlined with AI skills trained on historical edits, with both Greg (AAA’s Dispute Resolution Journal) and Nick (experts.com) building Claude skills from past redlines to automate first-pass editing, cite checking, and formatting. * AI-generated contract drafts without proper context or human review are creating nonsensical counterparty redlines, raising concerns about unreviewed AI negotiations and the emerging ethical threat of prompt injection in legal documents, which would likely violate Rule 8.4’s candor and dishonesty standards. * The shift to token and credit-based pricing by AI tools like Descript and Perplexity is pushing users toward alternatives, while Google’s announcement of shareable Gemini Notebooks in Workspace promises to transform how lawyers curate and share AI-assisted research with clients. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.legalailive.com

    (37) Legal AI Live, September 2026, Part 1

  2. Aug 26

    (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 over-romanticizing human judgment since many people have terrible taste. * AI is transforming education from elementary school through professional training: AI tools now provide personalized Socratic learning at scale, public schools are teaching AI literacy to third graders, and professionals like Nick are learning faster than ever, though universities remain stuck in medieval pedagogical models. * AI shaming is counterproductive and elitist: Drawing parallels to public health research, Kara Peterson argued that shaming people for using AI or making mistakes with it is self-defeating, and Jasmine Singh noted that in fast-paced environments, not using AI is the real problem. * Both coding and legal work are being abstracted away: Just as vibe coding lets non-technical users build software through plain English, legal services may similarly be abstracted so people get legal answers without recognizing their problems as legal, but expert architects remain essential to design the guardrails and governance around that abstraction. * Prompt injection is an emerging legal threat but may be solvable: Pro se litigants and lawyers have already attempted prompt injection through hidden white text in court filings, creating new duties for organizations to detect such attacks, though Anthropic announced that Claude can now reject prompt injections at the model level, suggesting the problem may diminish over time. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.legalailive.com

    (36) Legal AI Live, August 2026, Part 2

  3. Aug 19

    (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 68-year-old insurance professional with no coding background accidentally vibe-coded a working web app using Perplexity Pro, proving AI tools have become accessible enough for non-technical users to create functional software through plain English conversation. * Enterprises are shifting to deep agent delegation: Companies are moving beyond chat-based AI usage toward outsourcing entire workflows to agentic AI systems, driving a significant increase in enterprise token consumption. * AI can now self-improve recursively: Developers are building systems where one AI agent creates output and another validates and corrects it, making systems smarter over time but also less understandable to humans. * Human judgment and verification remain essential: While AI can handle roughly 80% of legal tasks better than humans, the remaining 20% requires human ethics and artistry, and attorneys who fail to verify AI-generated citations face real sanctions, with courts issuing $145,000 in Q1 alone for hallucinated cases. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.legalailive.com

    (35) Legal AI Live, August 2026, Part 1

  4. Aug 10

    (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 traditional “better, faster, cheaper” trade-off, enabling lawyers to produce higher-quality work product while simultaneously increasing efficiency and reducing costs. * The shift to usage-based efficiency: In response to “token scarcity,” legal tech is moving toward usage-based pricing models where AI systems orchestrate workflows by delegating tasks to the most cost-effective models. * Reimagining legal education: Legal pedagogy must integrate AI as a fundamental, experiential tool to prepare students for the modern realities of managing legal business systems and AI-assisted drafting. * Maintaining privilege and security: Attorney-client privilege and work product protections remain robust when using enterprise-grade AI tools, as contractual confidentiality agreements create a reasonable expectation of privacy comparable to traditional communication methods. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.legalailive.com

  5. Jul 27

    (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 “tokenpocalypse”moving from subscription billing to metered/token-based AI usage is forcing lawyers to critically evaluate their hourly business model. * Workflow Integration over Chatbots: The legal field is evolving beyond simple AI chatbot queries toward integrating AI directly into workflows through tools that connect systems, pull context, and streamline tasks. * AI in Education and Practice: While some law schools are banning AI, professionals emphasize that students must learn to use these tools outside of coursework to remain competitive, and seasoned attorneys are finding success using AI to draft complex legal documents. * Democratizing Legal Practice: AI tools are lowering the barriers to entry for starting a law practice, enabling solos and small firm attorneys to build websites, manage billing, and draft documents with unprecedented speed and independence. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.legalailive.com

  6. Jun 29

    (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 crisis. As clients refuse to pay for junior work and firms automate routine tasks, there’s a real unresolved question about how new lawyers develop judgment and discernment without the traditional “cut your teeth” experiences. * AI in legal education needs guardrails, not bans. Law schools are shifting from banning AI to teaching students how to critically evaluate AI output. The goal is developing judgment alongside using the tools, not instead of using them. * Agentic workflows are the current frontier. Mathew’s Comet browser workflow (chaining a legal analysis AI with a document AI assistant to auto-redline contracts) exemplifies where practical AI use is heading: multi-model, multi-step automation without burning tokens on unnecessary heavy models. * Big Law’s AI investments may not align with the profession’s future. Kirkland & Ellis spending $500M on a proprietary model reflects a for-profit firm optimizing for its own margins, not for how the next generation of lawyers should be developed. The profession needs to think critically about whose vision of the future it’s building toward. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.legalailive.com

    (32) Legal AI Live, June 2026, Part 2

  7. Jun 22

    (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 problem, its a competency problem. Cat Moon and Cat Casey both pushed back on the “lawyers screwing up with AI” narrative: human hallucinations predate ChatGPT. The real issue is a long-standing failure to hold lawyers accountable for competency, and AI is finally forcing that reckoning. * Discernment is the critical skill, not tool fluency. Cat Moon’s upcoming AI competency framework centers discernment, the lawyerly judgment to critically evaluate AI output, above AI literacy or tool use. You can’t outsource judgment; it has to be formed through doing the actual work. * Banning AI in law schools is the wrong move but using it uncritically is worse. The panel agreed that banning AI (as Berkeley attempted) does students a disservice, especially those with learning differences. But the goal should be teaching lawyers to use AI in context, verifying citations and checking reasoning, not just accepting polished output. * OpenAI’s Codex for law and Big Law’s $500M AI bets are a wake-up call. The former Ironclad CEO moving to OpenAI to build a law-specific model, alongside Kirkland & Ellis spending $500M on AI, signals a foundational shift. AI-native law firms and private equity in legal are happening fast, and anyone not paying attention risks being left behind. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.legalailive.com

    (31) Legal AI Live, June 2026, Part 1

  8. Jun 1

    (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 false dichotomy. Tools like MikeOSS aren’t eating Harvey’s or Legora’s lunch; they’re expanding the market to users who could never afford enterprise licenses. Different tools serve different addressable markets. * Vibe coding is accessible but unpredictable. Mathew built a custom app using Perplexity in ~3 hours for $15, orchestrating AI tools against each other. The cost and time savings are real, but the process is nonlinear and can break. * Human taste and expertise still matter. AI output is “pretty good,” but the value-add is curation and judgment (Nick’s 83-year-old father reviewing an AI-drafted lease addendum). The shift may be toward “service as a service” — humans guiding AI rather than just using software. * AI is transforming education. Nick highlighted that AI has made learning more accessible than ever, particularly for people with learning differences like dyslexia, calling it the best educational experience of his life. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.legalailive.com

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Ratings & Reviews

5
out of 5
3 Ratings

About

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

Information

  • Creator
    Mathew Kerbis, The Subscription Attorney
  • Years Active
    2025 - 2026
  • Episodes
    37
  • Rating
    Clean
  • Copyright
    © 2025-2026 Kerbisverse LLC. All rights reserved.
  • Show Website
    Legal AI Live

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