The Tech Savvy Lawyer Podcast By Michael D.J. Eisenberg cover art

The Tech Savvy Lawyer

The Tech Savvy Lawyer

By: Michael D.J. Eisenberg
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The Tech Savvy Lawyer interviews Judges, Lawyers, and other professionals discussing utilizing technology in the practice of law. It may springboard an idea and help you in your own pursuit of the business we call "practicing law". Please join us for interesting conversations enjoyable at any tech skill level!© ℗ 2020 Michael D.J. Eisenberg Politics & Government
Episodes
  • 🎙️ Ep. #134 — AI-Powered Legal Writing: How BriefCatch Helps Lawyers Write Smarter, Not Harder with Ross Guberman.

    🎙️ Ep. #134 — AI-Powered Legal Writing: How BriefCatch Helps Lawyers Write Smarter, Not Harder with Ross Guberman.
    Mar 31 2026
    My next guest is Ross Guberman — founder of BriefCatch, nationally recognized legal writing trainer, and author of several acclaimed books on persuasive legal writing. Ross has trained thousands of lawyers and judges across the country. After years of teaching the craft of legal writing, he channeled that expertise into building BriefCatch — a purpose-built AI writing tool that lives right inside Microsoft Word and Outlook, scanning your legal documents using roughly 17,000 rules to help you write cleaner, sharper, and more persuasive work product. Whether you're a solo practitioner or part of a large firm, Ross brings insights that are immediately practical — no matter your tech comfort level. 🚀 Join Ross Guberman and me as we discuss the following three questions and more! 🏆 From your vantage point — having trained thousands of lawyers and judges and now running BriefCatch — what are the top three ways lawyers can leverage AI-driven writing tools like BriefCatch inside Word and Outlook to measurably improve the quality and persuasiveness of their briefs without sacrificing their own voice or judgment?⚖️ For a tech-curious but time-strapped practitioner, what are the top three everyday workflows beyond traditional brief writing where lawyers are leaving the most value on the table by not using tools like BriefCatch and other legal tech?🔮 Looking ahead five years, what are the top three technology competencies every lawyer must develop — not just "nice to have" skills — to collaborate effectively with AI, stay ethically compliant, and turn technology into a genuine competitive advantage rather than a source of risk? In our conversation, we cover the following: [00:30] 💻 Ross's current tech setup — MacBook Pro M4 Max, macOS, and iPhone 16[01:30] 🔄 Why keeping your OS updated matters — security and performance[03:00] 🖥️ External monitors, portable screens, and traveling with tech[07:00] 📱 Using your iPad as an external monitor via Apple Sidecar[08:30] 🎪 Bonus Question #1 - Ross's experience in the ABA TECHSHOW Startup Alley[11:00] ✍️ Question #1 — Top 3 ways to use AI writing tools to improve briefs without losing your voice[12:00] 🧑‍⚖️ Using AI to role-play as a skeptical judge or opposing counsel to pressure-test your brief[13:00] 📊 Transforming fact sections into timelines and case law into comparison charts[14:00] 📝 Using AI as a self-check for hyperbole, redundancy, and tone[15:30] 📲 How judges now read briefs on iPads — and what that means for your writing style[17:00] 📂 Using Text Expander to store and deploy your best prompts[18:30] 🎙️ Google Notebook LLM as a learning and podcast creation tool[20:00] 🧩 Bonus Question #2 — What is BriefCatch and why use purpose-built legal AI over general tools?[21:00] 🚀 The origin story of BriefCatch — from side hustle in 2018 to funded legal tech startup[22:30] ⚙️ Workflow, ethics rules, and attorney-specific conventions — why legal-specific AI wins[24:30] 📋 Question #2 — Top 3 underused everyday workflows for lawyers using AI[25:00] 📧 Using AI with your email to surface unanswered messages and unresolved threads[25:45] 📁 Mining your past work product for patterns, style, and reusable language[26:30] 📅 Having AI review your calendar and correspondence for efficiency insights[27:00] 🔒 Data privacy, security settings, and the risks of default AI configurations[28:30] 🏛️ New York State's data protection approach and what more states should do[29:30] 🤖 Question #3 — Top 3 technology competencies every lawyer must master in the next five years[30:00] 🧠 Understanding how LLMs actually "think" — reading the AI's reasoning chain[30:45] 🖊️ Making AI output sound like you — the human voice in an AI-generated world[31:30] 🔧 Integrating AI into your daily workflow while preserving human judgment[32:00] 👏 Closing thoughts and where to find Ross and BriefCatch Resources 🔗 Connect with Ross Guberman 📧 Email: ross@briefcatch.com🌐 Website: https://www.briefcatch.com💼 LinkedIn: Search "Ross Guberman" on LinkedIn at https://www.linkedin.com 📌 Mentioned in the Episode 🎤 ABA TECHSHOW — Annual legal technology conference hosted by the American Bar Association: https://www.techshow.com/🎤 ABA TECHSHOW Startup Alley — Competition for early-stage legal tech startups at ABA TECHSHOW: https://www.techshow.com/sessions/startup-alley/⚖️ Anthropic / Defense Department data privacy discussion — https://time.com/article/2026/03/16/your-data-pentagon-battle-with-anthropic/🗒️ Google Notebook LLM — AI-powered note-taking and audio podcast generation tool: https://notebooklm.google.com📰 Legal Week New York — Premier legal industry conference: https://www.event.law.com/legalweek🎙️ Mac Geek Gab Podcast (Dave Hamilton, Pilot Pete & Adam Christiansons): https://www.macgeekgab.com🎙️ Mac Power Users Podcast (...
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    34 mins
  • 🎙️ Ep. #133 | AI Search, GEO & Legal Marketing Tech: How Small Law Firms Win Cases — Not Just Clicks!

    🎙️ Ep. #133 | AI Search, GEO & Legal Marketing Tech: How Small Law Firms Win Cases — Not Just Clicks!
    Mar 17 2026
    My next guest is Nick Cohen, Chief Operating Officer of Matador Solutions — a legal marketing think tank and agency — and a newly minted partner at Cohen Injury Law Group. Nick brings a rare dual perspective: he lives the daily grind of running a law firm AND helps over 170 firms across the country use technology and marketing strategy to grow their practice. With more than $1 billion in case value generated for clients, Nick knows what separates the law firms that thrive from the ones that spin their wheels. 🚀 Whether you are just hanging out your shingle or you have been practicing for years and feel overwhelmed by the alphabet soup of SEO, GEO, PPC, and AI, this episode breaks it all down in plain language. Nick shares actionable steps — some of which cost nothing — to help your firm show up where your next great client is already looking. ⚖️ Join Nick Cohen and me as we discuss the following three questions and more! 🤔 What are the top three ways a small or mid-size law firm can leverage AI-driven search — like Google AI Overviews and ChatGPT — to reliably generate better cases, not just more clicks?💡 For firms that feel overwhelmed by SEO, paid search, and social media, what are the top three pieces of marketing technology or automations they should implement first to turn their website into a true new case acquisition system?🏆 Looking across $1 billion+ in case value generated for over 170 law firms, what are the top three technology habits the most successful firms share — and what are their less successful peers simply not doing? In our conversation, we cover the following: [0:00] 🎤 Introduction & five-star review shoutout[0:45] 👨‍💼 Nick's background: Matador Solutions, Cohen Injury Law Group, and tech stack overview (Jira, Google Suite, Claude, ChatGPT, WordPress, Slack)[1:30] 💻 Hardware setup: MacBook Pro M4, desktop, HDMI monitor — what Nick runs on daily[3:00] 📱 iPhone, planned obsolescence, and the Apple ecosystem slowdown conversation[4:00] ❓ Question 1: Leveraging AI-driven search (Google AI Overviews, ChatGPT) to get better cases — not just traffic[5:00] 🔍 GEO vs. SEO explained — what is Generative Engine Optimization and why it matters for your law firm right now[6:30] 📖 The difference: SEO = Google ranking; GEO = getting cited by ChatGPT, Claude, Perplexity, and Grok[8:00] 🤖 Schema markup, robots.txt, and opening your website to LLM crawlers — practical steps any firm can take[9:00] 📋 Attorney directory listings (Avvo, Super Lawyers, FindLaw) — are they worth the money in 2026?[10:30] ✍️ Tip #2: High-quality thought leadership content as a GEO and SEO powerhouse[11:30] ⭐ Tip #3: Reviews, reviews, reviews — the single highest-ROI, zero-cost activity for any law firm[12:00] 📲 The "one-click review link" strategy: why text beats email every time[13:00] 😬 How to handle negative reviews — call first, respond professionally, and why a 4.9 rating beats a perfect 5.0[15:00] ❓ Question 2: Top three marketing tech tools/automations for overwhelmed firms — CallRail, case management software, and understanding your channels[17:30] ❓ Question 3: The technology habits that separate high-growth firms from stagnant ones — intake systems, engagement, and growth mindset[19:30] 🗺️ How Matador Solutions walks a brand-new firm from zero to a steady stream of cases — step by step[22:00] 📬 Where to find Nick Cohen Resources 🔗 Connect with Nick Cohen 📧 Email: nick@matadorsolutions.net💼 LinkedIn: https://www.linkedin.com/in/nickecohen/🌐 Website: matadorsolutions.net 📚 Mentioned in the Episode (Non-Hardware / Non-Software) 🎙️ Apple Podcasts — podcasts.apple.com ⚖️ Matador Solutions — Legal marketing agency — matadorsolutions.net📋 Avvo — Attorney directory — avvo.com⚖️ Cohen Injury Law Group — Nick's law firm — https://cohenandcohen.net/⭐ Facebook Reviews — facebook.com📊 GEO (Generative Engine Optimization) — The emerging discipline of optimizing for AI-driven search engines⭐ Google Reviews — google.com/business📋 FindLaw — Attorney directory — findlaw.com📋 Super Lawyers — Attorney directory — superlawyers.com⭐ Yelp — yelp.com 💻 Hardware Mentioned in the Conversation 📱 Apple iPhone 15 — Nick's smartphone (approximate model) — apple.com/iphone📱 Apple iPhone (latest, annual upgrade) — Michael's smartphone — apple.com/iphone🖥️ Apple Mac Studio (M3 chip) — Michael's desktop — apple.com/mac🖥️ Apple MacBook Pro (M4 chip) — Nick's primary laptop — apple.com/macbook-pro ☁️ Software & Cloud Services Mentioned in the Conversation 📞 CallRail — Call tracking & marketing ROI — callrail.com🤖 ChatGPT (OpenAI) — AI assistant & AI search — chatgpt.com🤖 Claude (Anthropic) — AI assistant — claude.ai🤖 ...
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    24 mins
  • TSL.P Labs 🧪 Initiative: Why 96% AI Accuracy Still Fails Lawyers: Ethics, Hallucinations, and the Future of the Billable Hour ⚖️🤖

    TSL.P Labs 🧪 Initiative: Why 96% AI Accuracy Still Fails Lawyers: Ethics, Hallucinations, and the Future of the Billable Hour ⚖️🤖
    Mar 6 2026
    📌 To Busy to Read This Week's Editorial? Welcome to the TSL Lab's Initiative. 🤖 This weeks episode builds on my March 3rd, 2026, editorial "Even Though AI Hallucinations Are Down: Lawyers STILL MUST Verify AI, Guard PII, and Follow ABA Ethics Rules ⚖️🤖" is a misleading comfort blanket for lawyers, and how ABA Model Rules on confidentiality, competence, diligence, candor, supervision, and client communication must govern every AI prompt you run. Our Google LLM Notebook hosts translate the theory into practical workflows you can implement today—from document grounding and tokenization to vendor due diligence and line‑by‑line verification—so you can leverage AI confidently without sacrificing ethics, privilege, or your professional license. You will hear how document grounding changes what LLMs actually do, why uploading active case files to cloud AI tools can quietly trigger Rule 1.6 problems, and how cross‑border data flows, vendor training rights, and retention policies can erode privilege if you do not negotiate them carefully. 🔐 We also unpack practical safeguards like tokenization, internal sandbox testing, and bright‑line "danger zones" where AI must never operate unsupervised—especially on open‑ended research, choice of law, and any task that turns statistical text into real‑world legal risk. Finally, we confront the economic paradox: when AI can compress 100 hours of document review into seconds, but partners must still verify every line to protect their licenses, what exactly are clients paying for—and how does the billable hour survive? 💼 👉 Tune in now to learn how to stay tech‑forward without becoming the next ethics cautionary tale, and start designing AI policies that actually protect your clients, your firm, and your bar license. In our conversation, we cover the following 00:00 – Why "96% fewer hallucinations" is still not good enough in law ⚖️01:00 – How the remaining 4% error rate can trigger malpractice, sanctions, and ethics violations02:00 – From IT issue to ethics issue: ABA Model Rules as the real constraint on AI adoption03:00 – Document grounding 101: turning a free‑floating LLM into a reading‑comprehension engine04:00 – The hidden danger of "just upload the file": how Rule 1.6 confidentiality is instantly implicated05:00 – Cloud AI architecture, cross‑border data transfers, GDPR, and privilege risk 🌐06:00 – Model training nightmares: when your client's trade secrets leak back out through someone else's prompt07:00 – Negotiating no‑training clauses and ring‑fencing vendor data use (before you upload anything)08:00 – Tokenization explained: turning John Doe into "Plaintiff 01" without losing legal meaning 🔐09:00 – What AI does well today: grounded summarization, clause extraction, and playbook‑based redlines10:00 – The "danger zone" of tasks: open‑ended research, choice of law, and abstract legal reasoning11:00 – Phantom case law: how LLMs manufacture perfect‑looking but fake citations (and Rule 3.3 candor)12:00 – Sandboxing AI tools internally and measuring real‑world failure rates against known outcomes 🧪13:00 – Building bright‑line firm policies around forbidden AI use cases14:00 – Verification as a workflow, not a suggestion: what Model Rules 5.1 and 5.3 demand from supervisors15:00 – The efficiency paradox: when partner‑level verification erases associate‑level time savings ⏱️16:00 – Making AI verification as routine as a conflict check in your practice17:00 – Falling hallucination rates, rising risk: why better AI can still make lawyers more vulnerable18:00 – Client communication under Rule 1.4: when and why clients may be entitled to know you used AI19:00 – "You can delegate the task, not the liability": Rule 1.2 and ultimate responsibility for AI‑assisted work20:00 – Treating every AI prompt and ToS as a potential ethics document 📝21:00 – The existential question: if AI drafts in seconds, what exactly are clients paying lawyers for?
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    24 mins
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