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/ <br/><br/><a href="https://www.legalailive.com?utm_medium=podcast">www.legalailive.com</a>
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5/13/2025
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July 27, 2026
<p>This Episode’s Top 5 Takeaways:</p><p>* <strong>Balancing Anxiety and Excitement:</strong> 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.</p><p>* <strong>The Shift in AI Billing:</strong> The “tokenpocalypse”moving from subscription billing to metered/token-based AI usage is forcing lawyers to critically evaluate their hourly business model.</p><p>* <strong>Workflow Integration over Chatbots:</strong> 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.</p><p>* <strong>AI in Education and Practice:</strong> 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.</p><p>* <strong>Democratizing Legal Practice:</strong> 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.</p> <br/><br/>This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit <a href="https://www.legalailive.com?utm_medium=podcast&utm_campaign=CTA_1">www.legalailive.com</a>
June 29, 2026
<p>* <strong>Right-size your AI tools</strong>. 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.”</p><p>* <strong>The junior lawyer pipeline is in crisis</strong>. 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.</p><p>* <strong>AI in legal education needs guardrails, not bans</strong>. 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.</p><p>* <strong>Agentic workflows are the current frontier</strong>. 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.</p><p>* <strong>Big Law’s AI investments may not align with the profession’s future</strong>. 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.</p> <br/><br/>This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit <a href="https://www.legalailive.com?utm_medium=podcast&utm_campaign=CTA_1">www.legalailive.com</a>
June 22, 2026
<p>* <strong>AI models keep leaping forward and lawyers need to keep up</strong>. 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.</p><p>* <strong>Hallucinations aren’t an AI problem, its a competency problem</strong>. 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.</p><p>* <strong>Discernment is the critical skill, not tool fluency</strong>. 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.</p><p>* <strong>Banning AI in law schools is the wrong move but using it uncritically is worse</strong>. 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.</p><p>* <strong>OpenAI’s Codex for law and Big Law’s $500M AI bets are a wake-up call</strong>. 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.</p> <br/><br/>This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit <a href="https://www.legalailive.com?utm_medium=podcast&utm_campaign=CTA_1">www.legalailive.com</a>
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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/ <br/><br/><a href="https://www.legalailive.com?utm_medium=podcast">www.legalailive.com</a>
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